有机催化的迈克尔-迈克尔级联反应：多取代色满的不对称合成。

Organocatalyzed Michael-Michael cascade reaction: asymmetric synthesis of polysubstituted chromans.

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.

出版信息

J Org Chem. 2013 Jul 5;78(13):6488-94. doi: 10.1021/jo400476b. Epub 2013 Jun 17.

DOI:10.1021/jo400476b

PMID:23751013

Abstract

An enantioselective cascade Michael-Michael reaction between chalcones enolates and nitromethane catalyzed by a bifunctional thiourea is developed. This reaction provides a mild but efficient approach to chiral benzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities, and the benzopyrans can be easily transformed to the corresponding tricyclic product.

摘要

手性双功能硫脲催化的查尔酮烯醇盐与硝基甲烷的对映选择性级联 Michael-Michael 反应被开发出来。该反应为手性苯并吡喃提供了一种温和但高效的方法，以高产率和优异的立体选择性得到含有三个连续立体中心的苯并吡喃，并且苯并吡喃可以很容易地转化为相应的三环产物。