Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 366181
Title Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems
Author(s) Sarabèr, F.C.E.; Dratch, S.; Bosselaar, G.; Jansen, B.J.M.; Groot, Æ. de
Source Tetrahedron 62 (2006)8. - ISSN 0040-4020 - p. 1717 - 1725.
DOI https://doi.org/10.1016/j.tet.2005.11.059
Department(s) Laboratory for Organic Chemistry
EPS-3
Publication type Refereed Article in a scientific journal
Publication year 2006
Keyword(s) silyl enol ethers - catalyzed conjugate addition - vitamin-d-3 northern portion - ring closure reactions - one-pot - acyclic stereoselection - titanium tetrachloride - 2+2+2 construction - carbonyl-compounds - organic-synthesis
Abstract Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated.
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