Catalytic Asymmetric Synthesis of Thiols

被引：58

作者：

Monaco, Mattia Riccardo ^{[1
]}

Prevost, Sebastien ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 49期

基金：

欧洲研究理事会;

关键词：

MESO-EPOXIDES; ENANTIOSELECTIVE ADDITION; CARBOXYLIC-ACIDS; DESYMMETRIZATION;

D O I：

10.1021/ja510069w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected beta-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.

引用

页码：16982 / 16985

页数：4

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