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The Mitsunobu Reaction: Origin, Mechanism, Improvements, and Applications

2007; Wiley; Volume: 2; Issue: 11 Linguagem: Inglês

10.1002/asia.200700182

1861-4728

Tracy Yuen Sze But, Patrick H. Toy,

Oxidative Organic Chemistry Reactions

The Mitsunobu reaction is a widely used and versatile method for the dehydrative oxidation-reduction condensation of an acid/pronucleophile usually with a primary or secondary alcohol that requires the combination of a reducing phosphine reagent together with an oxidizing azo reagent. The utility of this reaction stems from the fact that it is generally highly stereoselective and occurs with inversion of the stereochemical configuration of the alcohol starting material. Furthermore, as carboxylic acids, phenols, imides, sulfonamides, and other compounds can be used as the acid/pronucleophile, this reaction is useful for the preparation of a wide variety of functional groups. This Focus Review of the Mitsunobu reaction summarizes its origins, the current understanding of its mechanism, and recent improvements and applications.