手性N,N'-二氧化物-有机催化的区域、非对映和对映选择性迈克尔加成-烷基化反应

Chiral N,N'-Dioxide-Organocatalyzed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction.

作者信息

Feng Juhua, Yuan Xiao, Luo Weiwei, Lin Lili, Liu Xiaohua, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.

College of Science, Sichuan Agricultural University, Ya'an, Sichuan, 625014, P. R. China.

出版信息

Chemistry. 2016 Oct 24;22(44):15650-15653. doi: 10.1002/chem.201603629. Epub 2016 Sep 30.

DOI:10.1002/chem.201603629

PMID:27690271

Abstract

A highly regio-, diastereo- and enantioselective Michael addition-alkylation reaction between α-substituted cyano ketones and (Z)-bromonitrostyrenes has been realized by using a chiral N,N'-dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2,3-dihydrofurans were obtained in up to 95 % yield with 95:5 dr and 93 % ee.

摘要

通过使用手性N,N'-二氧化物作为有机催化剂，实现了α-取代氰基酮与(Z)-溴硝基苯乙烯之间高度区域选择性、非对映选择性和对映选择性的迈克尔加成-烷基化反应。多种底物在该反应中表现良好，以高达95%的产率、95:5的非对映体比例和93%的对映体过量获得了相应的多官能化手性2,3-二氢呋喃。