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 496949
Title Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions
Author(s) Hoogenboom, Jorin; Zuilhof, Han; Wennekes, Tom
Source Organic Letters 17 (2015)22. - ISSN 1523-7060 - p. 5550 - 5553.
DOI https://doi.org/10.1021/acs.orglett.5b02662
Department(s) Laboratory for Organic Chemistry
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2015
Abstract

A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.

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