Chiral N,N'-Dioxide-Organocatalyzed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction.
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.
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.
Juhua
J
Feng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Xiao
X
Yuan
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Weiwei
W
Luo
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. lililin@scu.edu.cn.
Lili
L
Lin
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Xiaohua
X
Liu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. xmfeng@scu.edu.cn.
Xiaoming
X
Feng
2,3-dihydrofuran; Michael alkylation; asymmetric catalysis; chiral N,N′-dioxide; organocatalysis