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    About

Synlett

Thieme

1989-

ISSN: 0936-5214 (1437-2096)
Chemistry, Organic - Organic Chemistry
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Recent articles

1 show abstract
2018-02-08T00:00:00+0100
Authors: Sun ; Kehuan ; Long ; Bohua ; Jin ; Yu ; Zhu ; Xiaofeng ; Zhang ; Jingzhao ; Wang ; Xueyan ; Tang ; Xudong ; Wu ; Zhengzhi ; Zhang ; Ronghua
Article URL: http://dx.doi.org/10.1055/s-0036-1591928
Citation: Synlett ; : -
Publication Date: 2018-02-08T00:00:00+0100
Journal: Synlett
2 show abstract
2019-01-08T00:00:00+0100
The anodic C–C cross-coupling reaction provides fast access to a wide range of bi- and terarylic scaffolds by electrochemically mediated arylation reactions. Herein, a metal- and reagent-free electrosynthetic protocol for the synthesis of nonsymmetrical 2-hydroxy-para-teraryl derivatives is presented for the first time. It is scalable, easy to conduct, and allows the use of a broad variety of different functional groups.
3 show abstract
2019-01-14T00:00:00+0100
A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.
4 show abstract
2019-01-18T00:00:00+0100
β-Lactams are highly valuable compounds due to their antibiotic activity. Among the number of well-established methodologies for building this privileged scaffold, our research group has settled on a novel synthetic approach for their preparation. This Account focuses on our latest progress in the synthesis of these compounds through a novel base-promoted intramolecular cyclization of benzylfumaramide-based rotaxanes. The mechanical bond plays a significant role in the process by activating the cyclization inside the macrocycle void, avoiding the formation of byproducts and fully controlling the diastereoselectivity. Further investigations on this transformation led to the formation of ­enantioenriched 2-azetidinones. The cyclization of enantiopure interlocked α-methylbenzylfumaramides allows the formation of two new stereogenic centers in the lactamic four-membered ring, one of them a quaternary carbon, keeping the initial configuration of the chiral group of the starting material.1 Introduction1.1 Mechanically Interlocked Molecules and Applications1.2 Chemical Stabilization of the Mechanical Bond2 Literature Methods for 4-exo-trig Ring Closures of Fumaramides for the Synthesis of β-Lactams3 Our First Encounter with Interlocked β-Lactams3.1 An Unexpected Result in Our Laboratory3.2 Finding the Optimal Reaction Conditions3.3 Elucidating the Effects of the Mechanical Bond4 Diastereoselective Synthesis of Interlocked and Non-Interlocked β-Lactams5 Asymmetric Cyclization of Enantiopure Interlocked Fumaramides6 Conclusions
5 show abstract
2019-01-22T00:00:00+0100
2-Aminoallyl cations are reactive intermediates that undergo diverse reactions, such as cycloadditions, direct nucleophilic additions, Nazarov electrocyclizations, and rearrangements. We review recent development in asymmetric catalytic reactions (nucleophilic additions and Nazarov electrocyclizations) based on chiral counteranion-paired 2-aminoallyl cation intermediates generated through activation of α-hydroxy enamides in the presence of chiral Brønsted acid catalysts. With an understanding of their asymmetric catalysis modes and mechanisms, we expect more asymmetric catalytic reactions will be developed on the basis of this strategy in the near future.
6 show abstract
2019-02-06T00:00:00+0100
Structure elucidation using NMR spectroscopy has become a vital part of the toolkit of modern synthetic chemistry. Characterisation of final products, quality control of production, analysis of complex mixtures in synthetic method development, and structure elucidation of isolated natural products are examples where NMR spectroscopy is a part of daily routine. The two factors that usually limit the applicability of NMR are resolution and sensitivity. The experimental method described in this Account, real-time pure shift acquisition, yields heteronuclear correlation spectra such as HSQC that offer significant improvements in both resolution and sensitivity, at negligible cost to the analyst. The advantages that real-time pure shift acquisition enjoys over conventional experiments are discussed and illustrated with selected examples including carbohydrate and alkaloid mixtures. Advanced data acquisition and processing techniques that reduce experiment time and are easily combined with pure shift NMR methods are also described.1 Introduction2 Simultaneous Sensitivity and Resolution Enhancement Using Real-Time Acquisition in HSQC3 Processing Pure Shift Data4 Pulse Sequences for Real-Time Pure Shift HSQC5 Conclusions and Future Perspectives
7 show abstract
2019-02-05T00:00:00+0100
This account presents the synthesis and the characterization of triazine-tetrazine nitrogen heterocyclic compounds. Some compounds were characterized by NMR and IR spectroscopy, mass spectrometry, differential scanning calorimetry (DSC), and single-crystal X-ray diffraction. The physical and chemical properties were obtained by EXPLO5 v6.01, gas pycnometer, BAM Fallhammer, BAM Friction tester, and several detonation tests. The results show that the new metal-free polyazido compound 3,6-bis-[2-(4,6-diazido-1,3,5-triazin-2-yl)-diazenyl]-1,2,4,5-tetrazine (4) with high heat of formation (2820 kJ mol–1/6130.2 kJ kg–1) and excellent detonation velocity and pressure (D = 8602 m s–1, P = 29.4 GPa) could be used as ingredient in secondary explosives. 3,6-Bis-[2-(4,6-diazido-1,3,5-triazin-2-yl)-hydrazinyl]-1,2,4,5-tetrazine (3) can detonate research department explosive (RDX, cyclonite) as a primer (Δf
H
m = 2114 kJ mol–1/4555.2 kJ kg–1, D = 8365 m s–1, P = 26.8 GPa), whose initiation capacity is comparable to that of the traditional primary explosive Pb(N3)2. Therefore, the metal-free compound 3 can potentially replace lead-based-primary explosives, which would be advantageous for the environment.1 Introduction2 Strategies to Form High-Nitrogen Compounds with High Heat of Formation3 Metal-Free Strategies to Prepare Primary Explosives4 Concluding Remarks
8 show abstract
2019-02-05T00:00:00+0100
A convenient method for the synthesis of polyanilines was developed through the organoselenium-catalyzed oxidation of anilines with H2O2. Unlike reported methods, this reaction generates no wastes other than water. These green features make the method much more practical in terms of large-scale preparation. Moreover, it is the first example of an application of organoselenium catalysis techniques in aniline polymerization reactions and might be an important advance in the fields of both organoselenium catalysis and polyanilines.
9 show abstract
2019-02-08T00:00:00+0100
Aryldiazonium salts are widely used in many organic transformations with displacement of N2 or through addition to the terminal nitrogen. Such aryldiazonium salts can be viewed as N-based Lewis acids that can react with Lewis bases to synthesize a wide variety of azo compounds. Additionally, diazonium salts are known to undergo single-electron transfer and release N2, forming an aryl radical, which results in different reactivity. Herein, we provide a concise overview of the reactivity of aryldiazonium salts undergoing classical donor-acceptor reactivity or single-electron transfer.
10 show abstract
2019-02-07T00:00:00+0100
Na2SeSO3, which can be generated in situ by the reaction of Na2SO3 with Se power, was found to be an odorless reagent for the selenenylation of alkyl halides to produce dialkyl diselenides. These products have been recently shown to be good catalysts for the Baeyer–Villiger oxidation of carbonyl compounds, for the selective oxidation of alkenes, or for the oxidative deoximation of oximes. By using aqueous EtOH as the solvent and avoiding the generation of a malodourous selenol intermediate, the selenylation reaction with Na2SeSO3 is much more environmentally friendly than conventional methods. Owing to the cheap and abundant starting materials and selenium reagents, our novel synthetic method reduces the production costs of dialkyl diselenides as organoselenium catalysts, thereby advancing practical applications of organoselenium-catalysis technologies.
11 show abstract
2019-02-13T00:00:00+0100
We have demonstrated a Diels–Alder reaction of an o-quinone generated in an electrochemical flow microreactor. In the flow microreactor system, 4-tert-butyl-o-benzoquinone was easily electrogenerated from 4-tert-butylpyrocatechol in the absence of chemical oxidants and then rapidly used, without decomposing, in a subsequent Diels–Adler reaction with various fulvenes to give the desired products efficiently.
12 show abstract
2019-02-18T00:00:00+0100
A Ni-catalyzed enantioselective reductive diarylation of alkenes through a tandem Heck cyclization/cross coupling of two structurally distinguished aryl bromides is accomplished for the first time. This reaction takes place under very mild conditions with high efficiency and tolerates a variety of functional groups. Thus, it provides a rapid access to various medicinally relevant bis-heterocycles containing all-carbon quaternary centers with very high enantioselectivity.
13 show abstract
2019-02-21T00:00:00+0100
gem-Diborylalkanes serve as privileged carbanion precursors for the efficient construction of carbon–carbon bond with various carbonyl and carboxyl compounds. We highlight the recent advances on deoxygenative transformation of carbonyl and carboxyl compounds using gem-diborylalkanes reagents. Our recent development of a dual functionalization of gem-diborylalkanes through deoxygenative enolization with the carboxylic acids is also discussed.1 Introduction2 Activation Modes of gem-Diborylalkanes3 Deoxygenative Transformation of Carbonyl and Carboxyl ­Compounds via α-Diboryl Carbanion3.1 Reaction with Aldehyde and Ketone Electrophiles3.2 Reaction with Carboxylic Acid Derivatives4 Deoxygenative Transformation of Carbonyl and Carboxyl ­Compounds via α-Monoboryl Carbanion5 Conclusion
14 show abstract
2019-02-22T00:00:00+0100
The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.1 Introduction2 Synthesis of Aziridines3 Synthesis of Indoles and Indolizines4 Synthesis of Triazoles5 Synthesis of Imidazoles6 Synthesis of Oxazoles and Thiazoles7 Synthesis of Quinoxalines, Triazines, and Pyridines8 Conclusion and Outlook
15 show abstract
2019-02-26T00:00:00+0100
The controlled preparation of well-defined distorted nanographenes by a bottom-up approach based on organic synthesis permits the direct establishment of unprecedented structure–property relationships in carbon nanostructures. The simultaneous incorporation of various defects in nanographenes affords highly curved structures with novel or enhanced photophysical properties. In this sense, we recently reported a fully helical and saddle-shaped nanographene ribbon containing the first undecabenzo[7]helicene unit. Both its linear and nonlinear optical properties are enhanced in comparison with those of other partially π-extended [7]helicenes. Moreover, the new superhelicene exhibits the highest emission dissymmetry factor (g
lum) reported to date for a homochiral nanographene. The combination of both nonlinear and chiroptical properties in nanographenes opens up new possible future applications for those distorted nanostructures.1 Introduction2 Synthesis of Embedded Seven-Membered Rings3 Combination of Defects: Seven-Membered Rings and π-Extended Helicenes4 Conclusions and Outlook
16 show abstract
2019-03-01T00:00:00+0100
A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C–H bonds are converted into their C–F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.
17 show abstract
2019-03-12T00:00:00+0100
In this account we summarized our work on the modification and extension of the thiadiazoloquinoxaline (TQ) as a strong acceptor unit for organic electronics. While also alternating conjugated copolymers with different donors were published, the focus here is the description of variation of the acceptor unit leading to many small molecules with different electronic properties as indicated from their optical absorptions, cyclic voltammetry (CV) data, density functional theory (DFT), and time-dependent (TD-DFT) calculations. The extension with ortho-diquinones seemed a promising way to enlarge the TQ molecules and further increase their electron affinity. At the end it is demonstrated how these units can be merged with other acceptors like naphthalenediimide (NDI) and be extended in an iterative way to extremely long condensed pyrene-fused heteroacenes with TQ end groups just by ring opening of the thiadiazole five-membered ring followed by further condensations in an iterative way.1 Introduction2 The Synthesis of TQ Cores3 The Extension of TQ3.1 The Extension at 4,9-Positions3.2 The Extension at 6,7-Positions3.3 The Extension on NDI3.4 The Extension with TQ for Endcapping (Bis TQ)4 Conclusions
18 show abstract
2019-03-18T00:00:00+0100

Article URL: http://dx.doi.org/10.1055/s-0037-1612424
Citation: Synlett 2019; 30: V-
Publication Date: 2019-03-18T00:00:00+0100
Journal: Synlett
19 show abstract
2019-03-18T00:00:00+0100
Authors: Zanda ; Matteo
Article URL: http://dx.doi.org/10.1055/s-0037-1612158
Citation: Synlett 2019; 30: A32-A47
Publication Date: 2019-03-18T00:00:00+0100
Journal: Synlett
20 show abstract
2019-03-19T00:00:00+0100
The reagent system comprised of halotrimethylsilane and nitrite or nitrate salts has now been successfully used as an efficient system for a series of versatile synthetic transformations. In recent years, the significance and efficacy of this system for reactions such as nitration of aromatics and olefins, oxidation of thiols to sulfonyl chlorides, ipso-nitrosation/nitration of arylboronic acids, ipso-nitration of α,β-unsaturated carboxylic acids to nitro olefins, etc. have been disclosed. Though the reagent system has not been exploited to its full potential, the reported reactions reveal its advantages as a very safe and convenient system that works under mild conditions. This brief Account reveals various synthetic applications of halotrimethylsilane-nitrite/nitrate salts in organic synthesis hitherto reported.1 Introduction2 Reactions Using a Halotrimethylsilane-Nitrate Salt System2.1 Nitration of Olefins and Aromatics2.2 One-Pot Preparation of gem-Chloronitroso, gem-Chloronitro, and vic-Dichloro Compounds2.3 One-Step Conversion of Anilines into Haloarenes2.4 Deoximation of Aldoximes to Aldehydes and Ketoximes to ­Ketones2.5 One-Pot Synthesis of Cyclic/Noncyclic α-Nitroketones from ­Cyclic/Noncyclic Olefins2.6 ipso-Nitration of Arylboronic Acids2.7
ipso-Nitrosation of Arylboronic Acids2.8 Oxidation of Sulfides and Sulfoxides to Sulfones2.9 Oxidative Chlorination of Thiols and Disulfides to Sulfonyl ­Chlorides2.10

α-Halogenation of Carbonyl Compounds2.11 Decarboxylative ipso-Nitration and Dibromination of Cinnamic Acid3 Conclusion
21 show abstract
2019-03-19T00:00:00+0100
Our endeavors in the design, realization and application of a formal anti-carbopalladation of alkynes are summarized. Whereas numerous examples of syn-carbopalladation steps embedded in cascade reactions are known, there have been almost no examples of the corresponding anti-carbopalladation steps. From a personal perspective, this account provides insights on the original considerations and hypotheses, and their validation or invalidation by experimental and computational means. This account also aims at clarifying how different ideas have been developed and how novel reaction sequences paving the way to a plethora of different scaffolds have been designed. The reader will recognize the importance of the interplay between elucidating reaction mechanisms and developing novel methodologies. As a result, useful methods to create homo- and heterotetrasubstituted double bonds have been developed. The broad versatility of these methods has been demonstrated by a novel total synthesis of the indole alkaloid (+)-lysergol.1 Introduction2 Initial Studies3 Various Termination Steps4 Termination with Heteronucleophiles5 Natural Product Synthesis6 anti-Carbopalladations Realized by the Lautens Lab7 Conclusion and Outlook
22 show abstract
2019-03-19T00:00:00+0100
We describe the synthesis of ionic-liquid-supported 1,3-dimethylimidazolidin-2-one, together with the halogenation of alcohols in a reaction system in which this reagent is combined with oxalyl chloride. A new method was established that does not require additives such as bases, and which permits the ready isolation and purification of the product. Good conversions were obtained, and good reusability of the reagent was observed.
23 show abstract
2019-03-19T00:00:00+0100
A mild, efficient, and environmentally friendly method for the selective protection of secondary hydroxyl groups is described. The method involves the protection of both primary and secondary hydroxyl groups as tert-butyldimethylsilyl (TBDMS) ethers and selective deprotection of the primary TBDMS group with formic acid in acetonitrile/water. The rates of desilylation of primary and secondary TBDMS ethers by different concentrations of formic acid are determined. Formic acid of 5–20% concentration is found to selectively deprotect primary TBDMS ethers while keeping more than 95% of their secondary counterparts intact.
24 show abstract
2019-03-19T00:00:00+0100
Stereospecific generation of α-amino ketones from common α-amino acids is difficult to achieve, often employing superstoichiometric alkylating reagents and requiring multiple protecting group manipulations. In contrast, the α-oxoamine synthase protein family performs this transformation stereospecifically in a single step without the need for protecting groups. Herein, we detail the characterization of the 8-amino-7-oxononanoate synthase (AONS) domain of the four-domain polyketide-like synthase SxtA, which natively mediates the formation of the ethyl ketone derivative of arginine. The function of each of the four domains is elucidated, leading to a revised proposal for the initiation of saxitoxin biosynthesis, a potent neurotoxin. We also demonstrate the synthetic potential of SxtA AONS, which is applied to the synthesis of a panel of novel α-amino ketones.1 Introduction2 Native SxtA Module Activity3 New Reactions with SxtA AONS4 Conclusions and Outlook
25 show abstract
2019-03-19T00:00:00+0100
Carbon dioxide is arguably one of the most stable carbon-based molecules, yet enzymatic carbon fixation processes enabled the sustainable life cycle on Earth. Chemical reactions involving CO2-functionalization often suffer from low efficiency with highly reactive substrates. We recently reported mild carboxylation of aldehydes to furnish α-keto acids – a building block for chiral α-amino acids via reductive amination. Here, we discuss potential reaction mechanisms of aldehyde carboxylation reactions based on two promoters: NHCs and KCN in the carboxylation reaction. New DFT mechanistic studies suggested a lower reaction barrier for a CO2-functionalization step, implying a potential role of CO2 in prebiotic evolution of organic molecules in the primordial soup.1 Introduction: Aldehydes, Benzoins, Carboxylic Acids2 CO2-Activation: NHC, Cyanide, Lewis Acid and Water3 A Breslow Intermediate: Benzoin Reaction vs. Carboxylation with CO2
4 Carboxylation in the Primordial Soup5 Conclusion
26 show abstract
2019-03-19T00:00:00+0100
Deuterated compounds are of great importance in chemistry and pharmaceuticals. Reductive dehalogenation is one of the most useful methods to incorporate deuterium into molecules. This article briefly discusses the historical development of dehalogenative deuteration reactions that involve transition-metal catalysis, radical halogen abstraction, alkali-metal reductive deuteration, and the recently developed potassium methoxide/hexamethyldisilane-mediated dehalogenation of aryl halides.
27 show abstract
2019-03-26T00:00:00+0100
We report on the optimization of the alkoxylation of pyrrolidine-1-carbaldehyde by using a new electrochemical microreactor. Precise control of the reaction conditions permits the synthesis of either mono- or dialkoxylated reaction products in high yields.
28 show abstract
2019-03-26T00:00:00+0100
Rhodium(III)-catalyzed hydroarylation of terminal alkynes has not previously been achieved because of the inevitable oligomerization and other side reactions. Here, we report a novel Cp*Rh(III)-catalyzed hydroarylation of terminal alkynes in acetic acid as solvent to facilitate the C–H bond activation and subsequent transformations. This reaction proceeds under mild conditions, providing an effective approach to the synthesis of alkenylated heterocycles in high to excellent yields (31–99%) with a broad substrate scope (37 examples) and good functional-group compatibility. In this transformation, the loading of the alkyne can be reduced to 1.2 equivalents, which indicates the significant role of HOAc in lowering the reaction temperature and suppressing the oligomerization of the terminal alkyne. Preliminary mechanistic studies are also presented.
29 show abstract
2019-03-26T00:00:00+0100
An aqueous continuous-flow reaction system is developed for the palladium-catalyzed hydroxycarbonylation of aryl halides. Flow hydroxycarbonylation of aryl halides in aqueous solution proceeds efficiently in a flow reactor containing a palladium–diphenylphosphine complex immobilized on an amphiphilic polystyrene–poly(ethylene glycol) resin to give the corresponding benzoic acids in excellent yields.
30 show abstract
2019-03-26T00:00:00+0100
The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.1 Introduction2 Background: Umpolung Strategies for Preparing Chiral Amines3 Background: 2-Azadienes4 Reductive Couplings of 2-Azadienes5 Fluoroarylations of gem-Difluoro-2-azadienes6 Summary and Outlook
31 show abstract
2019-03-25T00:00:00+0100
We have studied for a long time the reaction of quinone acetal type compounds, such as quinone monoacetals, quinone O,S-acetals, and iminoquinone monoacetals, and have reported the regioselective introduction of various nucleophiles. Quinone monoacetals show various types of reactivities toward nucleophiles due to their unique structures. In this study, we found that aromatic and alkene nucleophiles can be regioselectively introduced into the α-position of the carbonyl group on quinone monoacetals by specific activation of the acetal moiety. These reactions enabled the metal-free synthesis of highly functionalized aromatic compounds by the regioselective introduction of nucleophiles. In this account, we describe our recent studies of the coupling of quinone monoacetals.1 Introduction2 Regioselective Introduction of Aromatic Nucleophiles into α-Position of Carbonyl2.1 Biaryl Synthesis by Introduction of Aromatic Nucleophiles2.2 Synthesis of Terphenyls and Oligoarenes by Iterative Coupling2.3 Synthesis of Phenol Cross-Coupling Products3 [3+2] Coupling with Alkene Nucleophiles3.1 Development of Efficient [3+2] Coupling3.2 Improvement of Brønsted Acid Promotor4 Synthesis of α-Aryl Carbonyl Compounds Triggered by Silyl Transfer5 Utilization of o-Quinone Monoacetals6 Application to Iminoquinone Monoacetals7 Conclusion
32 show abstract
2019-03-25T00:00:00+0100
The kinetics of the ring-opening polymerization of ε-caprolactone with butane-1,4-diol as the initiator and 1,5,7-triazabicyclo[4.4.0]dec-5-ene as catalyst were examined. A highly efficient and controllable polymerization of ε-caprolactone occurred with an activation energy of 22.5 kJ·mol–1, which is much lower than that observed with butan-1-ol as the initiator (39.5 kJ·mol–1). An intramolecular hydrogen-bonding-assisted mechanism is proposed to explain this lowering of the activation energy.
33 show abstract
2019-03-25T00:00:00+0100
The synthesis of 18F-perfluorinated motifs from [18F]fluoride is a non-trivial undertaking as highlighted by the few methods and range of motifs that are known. In this Synpacts article we highlight our recent work on the synthesis and derivatization of 1,1-18F-difluoroalkenes to expand the accessible radiochemical space with fluorine-18.1 Introduction2 Overview of the Main Strategies to Access 18F-Perfluorinated Motifs with [18F]Fluoride3 1,1-18F-Difluoroalkenes4 Conclusion
34 show abstract
2019-03-28T00:00:00+0100
A series of oligoarenes have been synthesized via sulfoxide-based iterative dehydrogenative transformations. By utilizing the sulfinyl moieties as on/off-switchable directing groups, overreactions and/or undesired oligomerizations were completely suppressed. Since the dehydrogenative couplings were not hampered by steric hinderance, sterically encumbered oligoarenes were synthesized.
35 show abstract
2019-04-02T00:00:00+01:00
Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion
36 show abstract
2019-04-02T00:00:00+01:00
The diphenyl diselenide catalyzed oxidative degradation of benzoin to benzoic acid is reported. As this reaction can convert the malodorous compound into an odorless and innocuous product under mild conditions, it might be useful for pollutant disposal. The reaction does not require a transition-metal catalyst or a chemical oxidant, so that it can be performed at low cost and without generation of wastes. This is believed to be the first example of the use of organoselenium catalysis technology in pollutant destruction, thereby expanding its range of applications.
37 show abstract
2019-04-02T00:00:00+01:00
A highly enantioselective arylation of 3-carboxamide oxoindoles with quinone monoimines is described. Various 3-aryl-3-carboxamide oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%) with moderate to good enantioselectivities (up to 98%) in the presence of a bifunctional thiourea-tertiary amine catalyst. The absolute configuration of one product was determined by an X-ray crystal structural analysis and the absolute configurations of the other products can be assigned by analogy. Moreover, several chiral spirooxindole-benzofuranones were synthesized from the 3-aryl-3-carboxamide oxindoles in moderate yields with moderate to good enantioselectivities.
38 show abstract
2019-04-02T00:00:00+01:00
A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.
39 show abstract
2019-04-08T00:00:00+01:00

Article URL: http://dx.doi.org/10.1055/s-0037-1611523
Citation: Synlett 2019; 30: V-
Publication Date: 2019-04-08T00:00:00+01:00
Journal: Synlett
40 show abstract
2019-04-08T00:00:00+01:00
Authors: Sambaiah ; M. ; Mallesham ; Poosa ; Shiva Kumar ; K. ; Bobde ; Yamini ; Hota ; Prasanta Kumar ; Yennam ; Satyanarayana ; Ghosh ; Balaram ; Behera ; Manoranjan
Article URL: http://dx.doi.org/10.1055/s-0037-1610871
Citation: Synlett 2019; 30: 868-868
Publication Date: 2019-04-08T00:00:00+01:00
Journal: Synlett
41 show abstract
2019-04-08T00:00:00+01:00
Authors: Hong ; Song ; Lu ; Yan ; Morita ; Masao ; Saito ; Shun ; Kobayashi ; Yuichi ; Jun ; Bokkyoo ; Bazan ; Nicolas G. ; Xu ; Xiaoming ; Wang ; Yapin
Article URL: http://dx.doi.org/10.1055/s-0037-1610872
Citation: Synlett 2019; 30: 868-868
Publication Date: 2019-04-08T00:00:00+01:00
Journal: Synlett
42 show abstract
2019-04-10T00:00:00+01:00
In this Account we present the total syntheses of artemisinin (an important antimalarial agent) and cyclopamine (the first natural inhibitor of the hedgehog signaling pathway). Furthermore, we describe the design and development of a γ-butyrolactone as an inhibitor of Gcn5 (a histone N-acetyltransferase), discuss the discovery of hyperforin and guttiferon G as the first natural products acting as inhibitors of sirtuins, and present the design of inhibitors of sialic acid biosynthesis. The biomedical background and importance are also discussed. Finally, we present the discovery and development of methods for transesterification, IBX-mediated oxidations, reduction of several functional groups with LiBH4/Me3SiCl, as well as a process enabling the synthesis of kilogram amounts of D-isocitric acid and its transformation to valuable chiral derivatives.1 Artemisinin and Malaria2 Cyclopamine and Cyclops3 Sunflowers, Krebs Cycle, and Isocitric acid4 Histones and N-Acetyltransferase Gcn55 St. John’s Wort, Hippocrates, and Sirtuins6 Sialic Acid and Inhibitors of Its Biosynthesis7 Transesterification8 IBX Reloaded9 And Finally: A Small Mistake with a Big Impact10 Epilogue
43 show abstract
2019-04-10T00:00:00+01:00
The electrochemical reduction of caffeine, never carried out previously, yielded in DMF–Et4NBF4 N-formyl-N,1-dimethyl-4-(methylamino)-1H-imidazole-5-carboxamide, a highly functionalized imidazole product derived from the opening of the uracil ring. This reactivity is different from that of the methylated salt of caffeine, the cathodic reduction of which leads to the opening of the imidazole ring. Moreover, the product obtained by cathodic reduction, formylated at the exocyclic amide nitrogen, is different from that formed by treatment in an aqueous solution of sodium hydroxide followed by formylation. The latter is formylated at the exocyclic amine nitrogen.
44 show abstract
2019-04-10T00:00:00+01:00
The first examples of early-transition-metal-catalyzed hydroaminoalkylation reactions of allenes are reported. Initial studies performed with secondary aminoallenes led to the identification of a suitable titanium catalyst and revealed that under the reaction conditions, the initially formed hydroaminoalkylation products undergo an unexpected titanium-catalyzed rearrangement to form the thermodynamically more stable allylamines. The assumption that this rearrangement involves a reactive allylic cation intermediate provides a simple explanation of the fact that no successful early-transition-metal-catalyzed hydroaminoalkylations of allenes have previously been reported. As a result of the generation of the corresponding cation, the titanium-catalyzed intermolecular hydroaminoalkylation of propa-1,2-diene unexpectedly gives an aminocyclopentane product formed by incorporation of two equivalents of propa-1,2-diene.
45 show abstract
2019-04-10T00:00:00+01:00
A Pd-catalyzed [3+2] cycloaddition reaction of vinylcyclopropane and trifluoromethyl ketones as well as α-keto esters were developed, affording tetrahydrofurans in high yield.
46 show abstract
2019-04-10T00:00:00+01:00
Strain-promoted azide–alkyne cycloadditions (SPAAC) are widely used for labeling azide-functionalized biomolecules in living cells but create mixtures of isomeric triazoles. We recently expanded the scope of SPAAC to the isomer-free generation of large functional molecules in living cells by designing the symmetrical pyrrolocyclooctynes PYRROC and SYPCO, which do not form isomers in SPAAC. Here, we present the synthesis and kinetic characterization of the cyclooctyne TRIPCO as a new reagent for isomer-free SPAAC (iSPAAC). TRIPCO was found to react faster than PYRROC and SYPCO in the [3+2] cycloaddition with benzyl azide.
47 show abstract
2019-04-10T00:00:00+01:00
A visible-light-mediated tandem sulfonylation/cyclization of vinyl azides with sulfonyl hydrazines was developed that provides an efficient and simple strategy for the synthesis of valuable 6-(sulfonylmethyl)phenanthridines with a broad substrate scope and satisfactory yields under mild conditions.
48 show abstract
2019-04-10T00:00:00+01:00
Cadogan reductive cyclization of substituted 2-aryl-3-nitropyridines to give δ-carbolines was performed under MoO2Cl2(DMF)2 catalysis with triphenylphosphine as a ligand. A new approach for the synthesis of the alkaloid quindoline based on a Mo(VI)-catalyzed Cadogan reductive cyclization of 2-phenyl-3-nitro-5,6,7,8-tetrahydroquinoline followed by aromatization of the resulting 2,3,4,10-tetrahydro-1H-indolo[3,2-b]quinoline is proposed. Various о-nitroarylpyridines, obtained by reacting acylpyruvates and cyclic hydroxymethylene ketones with nitroacetophenone enamines, were used as starting compounds for the preparation of δ-carbolines. The synthesized δ-carbolines were found to act as phosphors; their photophysical properties were studied and a structure–property relationship was revealed.
49 show abstract
2019-04-10T00:00:00+01:00
Sulfoxonium ylides have recently gained prominence as safe carbenoid precursors in metal-catalyzed reactions. The stability and reactivity of sulfoxonium ylides depend on the substitution of the ylide carbon. The reactivity of vinyl-substituted sulfoxonium ylides is different and offers several advantages over known stabilized sulfoxonium ylides in the case of carbenoid transfer reactions. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of sulfoxonium ylide-derived vinyl carbenoid transformations for N-Heterocycles.1 Introduction2 Classification of Sulfoxonium Ylides3 Synthesis of Vinyl Sulfoxonium Ylides4 [3+2] Annulation of Vinyl Sulfoxonium Ylides5 [4+1] Annulation of Vinyl Sulfoxonium Ylides6 Conclusion
50 show abstract
2019-04-12T00:00:00+01:00
Macrocycles and medium-sized rings have important applications in several scientific fields but can be challenging to make using traditional end-to-end cyclization reactions. Ring-expansion methods represent a useful alternative and offer numerous practical benefits. In this Account, we discuss the current state of the art of ring-expansion strategies that have been applied consecutively. Such methods have the power to expedite the design and synthesis of functionalized macro­cycles via the selective, iterative insertion of smaller fragments into ring-enlarged products.1 Introduction2 Insertion Reactions2.1 Transamidation/Transpeptidation2.2 Transesterification2.3 Transthioesterification2.4 Aminyl Radical Cascade2.5 Iterative Synthesis of Lactones2.6 Successive Ring Expansion of β-Ketoesters and Lactams3 Pericyclic Reactions3.1 Sulfur-Mediated Rearrangements3.2 Nitrogen-Mediated Rearrangements4 Fragmentation Reactions5 Conclusions and Future Outlook
51 show abstract
2019-04-12T00:00:00+01:00
The synthesis of two marine lipodipeptides, majusculamides A and B, is described. The key feature of this synthesis is the stereoselective construction of an α-methyl-β-keto-carboxamide moiety.
52 show abstract
2019-04-12T00:00:00+01:00
We report the decarbonylation of aldehydes through an aldehydic C–H bond cleavage catalyzed by a cationic iridium/bisphosphine catalyst. The reaction proceeds under relatively mild conditions to give the corresponding hydrocarbon products in moderate to high yields. In addition, this cationic iridium catalyst system can be applied to an asymmetric hydroacylation of ketones.
53 show abstract
2019-04-11T00:00:00+01:00
A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process.
54 show abstract
2019-04-11T00:00:00+01:00
A homocoupling reaction of 2-naphthols with formation of a C–O bond through electrochemical oxidative dearomatization in the presence of catalytic amounts of ferrocene and a ruthenium complex was developed. Mechanistic studies revealed that the reaction might proceed through coupling between two identical radical species. Moreover, a gram-scale experiment was performed to illustrate the potential practicability of this methodology in organic synthesis.
55 show abstract
2019-04-11T00:00:00+01:00
A novel method for preparing aromatic compounds containing cyclopropoxy via nucleophilic aromatic substitution reaction (SNAr) of fluoroaromatic compounds with cyclopropanol under relatively mild conditions is presented. As compared to the approaches reported previously for preparing 1-(cyclopropyloxy)-2-nitrobenzene, the one proposed in this work is simplified without sacrificing the yields: When the reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroaromatic compounds were employed as substrates for a test that proves a wide application scope of the method.
56 show abstract
2019-04-11T00:00:00+01:00
RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in nine steps, including the key step of organocatalytic asymmetric Diels–Alder reaction between acrolein and 1-benzyloxybutadiene.
57 show abstract
2019-04-16T00:00:00+01:00
We report a greener and more-general organic method for the synthesis of functional organic salts containing organic anions through a Schiff base reaction between readily available aldehydes and simple aminoguanidinium salts. This reaction is operationally simple, free of metal salts, and forms water as the sole byproduct. The broad scope and good functional-group compatibility of this method permit its use to provide ready access to a library of more than 70 distinct organic salts, including those of heterocyclic anions, complex pharmaceutical anions, and polyanions, which are difficult to obtain through classical inorganic methods. Moreover, choosing different aldehydes and organic anions provides a convenient method for modulating or improving the functional properties of the designed organic salts, such as their melting points, fluorescence, and energetic properties. We therefore expect that this method will open new opportunities for the discovery and functionalization of a wide variety of organic salts and functional materials.
58 show abstract
2019-04-16T00:00:00+01:00
As an extension of the study on the Hudrlik–Peterson reaction of trans-TMS-epoxy alcohols with lithium acetylides, four cis-TMS-epoxy alcohols possessing different alkyl substituents were subjected to the reaction with TMS-acetylide. The reaction completed in 1 h at 0 °C to afford cis-enynyl alcohols in good yields. The results indicated that cis-TMS-epoxy alcohols had higher reactivity than the trans-isomers. Anions derived from 1-heptyne and phenylacetylene participated in the reaction as well. The reaction was applied to optically active cis-TMS-epoxy alcohols, and the resulting enynyl alcohols were transformed to the synthetic intermediates of protectin D1, maresin 1, resolvin E1, and leukotriene B4.
59 show abstract
2019-04-16T00:00:00+01:00
Alkoxyl radicals are highly reactive species which rapidly react by hydrogen atom transfer (HAT) or β-fragmentation to afford a carbon-centered radical. We discuss herein how these RO· radicals can be efficiently trapped in an intermolecular manner by styrene derivatives when they are generated by photoredox catalysis from the corresponding N-alkoxypyridinium salts. This allows for the synthesis of valuable ethers with complete anti-Markovnikov regioselectivity.1 Introduction2 Anti-Markovnikov Alkoxylation of Alkenes: Background3 Addition of Alkoxyl Radicals to Styrenes4 Summary and Outlook
60 show abstract
2019-04-15T00:00:00+01:00
With the importance of sulfur-containing organic molecules, developing methodologies toward C–S bond formation is a long-standing goal, and, to date, considerable progress has been made in this area. Recent electrochemical oxidative cross-coupling reactions for C–S bond formation allow the synthesis of sulfur-containing molecules from more effective synthetic routes with high atom economy under mild conditions. In this review, we highlight the vital progress in this novel research arena with an emphasis on the synthetic and mechanistic aspects of the organic electrochemistry reactions.1 Introduction2 Electrochemical Oxidative Sulfonylation for the Formation of C–S Bonds2.1 Applications of Sulfinic Acid Derivatives for the Formation of C–S Bonds2.2 Applications of Sulfonylhydrazide Derivatives for the Formation of C–S Bonds3 Electrochemical Oxidative Thiolation for the Formation of C–S Bonds3.1 Applications of Disulfide Derivatives for the Formation of C–S Bonds3.2 Applications of Thiophenol Derivatives for the Formation of C–S Bonds4 Electrochemical Oxidative Thiocyanation for the Formation of C–S Bonds5 Electrochemical Oxidative Cyclization for the Formation of C–S Bonds6 Conclusion
61 show abstract
2019-04-15T00:00:00+01:00
An efficient process was developed for the perfluoroalkylation of N-arylacrylamides through an organocatalyzed photoredox/cyclization reaction of N-arylacrylamides with inexpensive perfluoroalkyl iodide reagents. The reaction employs an inexpensive organic dye, eosin Y, as the photoredox catalyst and is run under irradiation by a 26 W LED lightbulb.
62 show abstract
2019-04-15T00:00:00+01:00
Pyridine is a prevalent structural heterocyclic motifs in natural products, pharmaceuticals, and advanced materials. Several different methodologies have been developed for the synthesis of these kinds of molecules. However, a sustainable and efficient procedure for the synthesis of pyridines is still highly desirable. In this Synpacts article, we highlight our recent approach to the construction of highly substituted pyridines though a tandem condensation/alkyne isomerization/6π-3-azatriene electrocyclization sequence. The present protocol was used to synthesize a series of polysubstituted pyridines (30 examples) in moderate to good yields. The process also permitted the development of a concise strategy for collective total syntheses of suaveoline, norsuaveoline, and macrophylline.
63 show abstract
2019-04-18T00:00:00+01:00
In most electrochemical syntheses, reactions are happening at or near the electrode surface. For catalyzed reactions, ideally, the electrode surface would solely contain the catalyst, which then simplifies purification and lowers the amount of catalyst needed. Here, a new strategy involving phthalocyanines (Pc) to immobilize catalysts onto carbon electrode surfaces is presented. The large π structure of the Pc enables adsorption to the sp2-structure of graphitic carbon. TEMPO-modified Pc were chosen as a proof of concept to test the new immobilization strategy. It was found that the TEMPO-Pc derivatives functioned similarly or better than the widely used pyrene adsorption method. Interestingly, the new TEMPO-Pc catalyst appears to facilitate a cascade reaction involving both the anode and the cathode. The first step is the generation of an aryl aldehyde (anode) followed by the reduction of the aryl aldehyde in a pinacol-type coupling reaction at the cathode. The last step is the oxidation of a hydrobenzoin to create benzil. This work demonstrates the unique ability of electrochemistry and bifunctional catalysts to enable multistep chemical transformations, performing both reductive and oxidative transformations in one pot.
64 show abstract
2019-04-18T00:00:00+01:00
A diastereodivergent synthesis of N-substituted iminolactones by bromoiminolactonization of α-substituted α-allylmalonamides is reported. Whereas bromocyclization under conventional chemical conditions provided cis-bromoiminolactones, electrochemical conditions exhibited complementary diastereoselectivity to afford the trans-products. A variety of substituents on the nitrogen atoms and an α-position of the malonamide were tolerated under both sets of conditions to afford the corresponding iminolactones in excellent yields and high diastereoselectivities.
65 show abstract
2019-04-18T00:00:00+01:00
An Ugi four-component reaction was used to construct propargylamide starting materials for a subsequent domino Heck–Suzuki–Miyaura cross-coupling reaction to give derivatives of 4-benzylidene-1-oxo-3,4-dihydro-1H-isoquinoline.
66 show abstract
2019-04-18T00:00:00+01:00
A facile bisphosphorylation of amino-2-en-1-ones with trialkyl phosphites mediated by iron is developed. The reaction is considered to go through two Michael addition progresses. A variety of amino-2-en-1-ones are bisphosphorylated in high yields with functional group tolerance. In addition, the protocol of introduction of two different phosphates into one molecule is successful through a cascade reaction.

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Last updated: 2019-01-14

Impact

Journal Citation Reports (2017)

Impact factor: 2.369
Q2 (Chemistry, Organic (24/57))

Scopus Journal Metrics (2017)

SJR: 0.830
SNIP: 0.446
Impact (Scopus CiteScore): 0.187
Quartile: Q2
CiteScore percentile: 56%
CiteScore rank: 71 out of 163
Cited by WUR staff: 6 times. (2014-2016)

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