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

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

doi:10.1002/chem.201603629

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

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

Authors

Juhua Feng^{1

2}, Xiao Yuan¹, Weiwei Luo¹, Lili Lin³, Xiaohua Liu¹, Xiaoming Feng⁴

Affiliations

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
² College of Science, Sichuan Agricultural University, Ya'an, Sichuan, 625014, P. R. China.
³ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. lililin@scu.edu.cn.
⁴ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. xmfeng@scu.edu.cn.

PMID: 27690271
DOI: 10.1002/chem.201603629

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.

Keywords: 2,3-dihydrofuran; Michael alkylation; asymmetric catalysis; chiral N,N′-dioxide; organocatalysis.