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光延反应:起源、机理、改进及应用

The Mitsunobu reaction: origin, mechanism, improvements, and applications.

作者信息

But Tracy Yuen Sze, Toy Patrick H

机构信息

Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

出版信息

Chem Asian J. 2007 Nov 5;2(11):1340-55. doi: 10.1002/asia.200700182.

DOI:10.1002/asia.200700182
PMID:17890661
Abstract

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.

摘要

光延反应是一种广泛应用且用途多样的方法,用于酸/亲核试剂通常与伯醇或仲醇进行脱水氧化还原缩合反应,该反应需要将还原性膦试剂与氧化性偶氮试剂结合使用。此反应的实用性源于这样一个事实,即它通常具有高度的立体选择性,并且发生时起始醇原料的立体化学构型会发生反转。此外,由于羧酸、酚类、酰亚胺、磺酰胺和其他化合物都可用作酸/亲核试剂,该反应对于制备多种官能团很有用。这篇关于光延反应的重点综述总结了其起源、对其机理的当前理解以及最近的改进和应用。

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