Abstract
The Mitsunobu reaction involves the “redox” condensation of an acidic pronucleophile with a primary or secondary alcohol promoted by a reactive phosphonium salt derived from an alkyl or aryl phosphine and an azo compound. The synthetic utility of the reaction is demonstrated by the wide range of acidic pronucleophiles that are tolerated including carboxylic acids, phenols, imides, hydroxamates, thiols, thioamides, fluorinated alcohols, oximes, pyridinium and imidazolium salts, pyrimidine bases, β-ketoesters and trimethylmethane tricarboxylate (TMET) thereby generating a variety of functionally diverse molecules. The focus of this review is to highlight the recent development of new or alternative reagents and purification strategies for the Mitsunobu reaction with a discussion of their suitability for modern drug design supported by selected examples from the literature.
Current Organic Chemistry
Title: Recent Advances in the Mitsunobu Reaction: Modifications and Applications to Biologically Active Molecules
Volume: 13 Issue: 16
Author(s): Reynolds A. J. and Kassiou M.
Affiliation:
Abstract: The Mitsunobu reaction involves the “redox” condensation of an acidic pronucleophile with a primary or secondary alcohol promoted by a reactive phosphonium salt derived from an alkyl or aryl phosphine and an azo compound. The synthetic utility of the reaction is demonstrated by the wide range of acidic pronucleophiles that are tolerated including carboxylic acids, phenols, imides, hydroxamates, thiols, thioamides, fluorinated alcohols, oximes, pyridinium and imidazolium salts, pyrimidine bases, β-ketoesters and trimethylmethane tricarboxylate (TMET) thereby generating a variety of functionally diverse molecules. The focus of this review is to highlight the recent development of new or alternative reagents and purification strategies for the Mitsunobu reaction with a discussion of their suitability for modern drug design supported by selected examples from the literature.
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Cite this article as:
J. A. Reynolds and M. Kassiou, Recent Advances in the Mitsunobu Reaction: Modifications and Applications to Biologically Active Molecules, Current Organic Chemistry 2009; 13 (16) . https://dx.doi.org/10.2174/138527209789578144
DOI https://dx.doi.org/10.2174/138527209789578144 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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