有机催化反应中的 1,2-砜重排。

1,2-Sulfone rearrangement in organocatalytic reactions.

机构信息

Department of organic chemistry, University of Geneva Quai Ernest Ansermet 30, 1211 Geneva, Switzerland.

出版信息

Org Biomol Chem. 2011 Mar 7;9(5):1407-18. doi: 10.1039/c0ob00818d. Epub 2011 Jan 7.

Abstract

The 1,2-sulfone rearrangement resulting from nucleophilic addition to bis activated vinyl-sulfones has been studied in more detail. Various nucleophiles activated by different types of catalysts (enamine, Brönsted base, thiourea) are able to promote such rearrangement in excellent yields and moderate to excellent enantioselectivities (up to 94% ee). Mechanistic studies have led to a better understanding of the mechanism and allowed its application to other electrophiles such as vinyl-sulfone acrylates.

摘要

双活化乙烯砜的亲核加成导致的 1,2-砜重排已被更详细地研究。各种由不同类型的催化剂（烯胺、布朗斯台德碱、硫脲）活化的亲核试剂能够以优异的收率和中等至优异的对映选择性（高达 94%ee）促进这种重排。机理研究使人们对反应机理有了更好的理解，并允许将其应用于其他亲电试剂，如乙烯砜丙烯酰胺。