From Allylic Sulfoxides to Allylic Sulfenates: Fifty Years of a Never-Ending [2,3]-Sigmatropic Rearrangement

被引：57

作者：

Colomer, Ignacio ^{[1
]}

Velado, Marina ^{[1
]}

Fernandez de la Pradilla, Roberto ^{[1
]}

Viso, Alma ^{[1
]}

机构：

[1] CSIC, Inst Quim Organ Gen, Consejo Super Invest Cient, Juan Cierva 3, E-28006 Madrid, Spain

来源：

CHEMICAL REVIEWS | 2017年 / 117卷 / 24期

关键词：

2,3 SIGMATROPIC REARRANGEMENT; DIELS-ALDER REACTIONS; ENANTIOMERICALLY PURE DIASTEREOMERS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSELECTIVE TOTAL SYNTHESES; METHYLENE-GAMMA-BUTYROLACTONES; MISLOW-EVANS REARRANGEMENT; ASYMMETRIC TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS;

D O I：

10.1021/acs.chemrev.7b00428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The [2,3]-sigmatropic rearrangement of allylic sulfoxides to allylic sulfenates is a reversible process, generally shifted toward the sulfoxide. In the presence of thiophiles, the sulfenate is trapped, and allylic alcohols are obtained under mild conditions. In most cases, a good transfer of stereochemical information through an ordered transition state is obtained. Furthermore, the ease of coupling this process with other versatile, stereocontrolled reactions has enhanced the usefulness of this protocol. This review aims to provide a comprehensive survey of this rearrangement and its application in the synthesis of natural and bioactive products.

引用

页码：14201 / 14243

页数：43

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