Meldrum's 酸衍生受体的实用不对称共轭炔基化：手性β-炔基酸的获得。

Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.

机构信息

Department of Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA.

出版信息

J Am Chem Soc. 2010 Jan 20;132(2):436-7. doi: 10.1021/ja909105s.

DOI:10.1021/ja909105s

PMID:20020682

Abstract

The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors using cinchonidine (<$100/kg) as the chiral mediator. The process provides practical access to chiral beta-alkynyl acids. Noteworthy attributes of the method are its broad scope, high functional-group compatibility, and ease of scalability.

摘要

手性炔基亲核试剂的对映选择性共轭加成一直是合成化学中的一个长期挑战。本文描述了使用金鸡纳碱（<$100/kg）作为手性介体，对 Meldrum's 酸衍生受体进行高效实用的不对称共轭炔基化反应。该方法为手性β-炔基酸提供了实用的合成途径。该方法具有广泛的适用范围、高官能团兼容性和易于扩大规模等特点。