通过氮杂-Baylis-Hillman 反应实现亚胺、烷基乙烯酮和酰亚胺的有机催化串联三组分反应。

Organocatalytic tandem three-component reaction of imine, alkyl vinyl ketone, and imide via aza-Baylis-Hillman reaction.

机构信息

Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China.

出版信息

J Org Chem. 2011 Apr 15;76(8):2888-91. doi: 10.1021/jo102143r. Epub 2011 Mar 14.

DOI:10.1021/jo102143r

PMID:21401084

Abstract

A highly chemoselective PPh(3)-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.

摘要

发展了一种高化学选择性的 PPh(3)催化的三组分反应，涉及亚胺、烷基乙烯酮和邻苯二甲酰亚胺或琥珀酰亚胺。通过芳基亚胺和烷基乙烯酮的aza-Morita-Baylis-Hillman 反应，以及随后的酰亚胺的迈克尔加成和差向异构化，可以生成各种具有高立体选择性的高官能化加合物。