Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines.
A highly efficient N,N'-dioxide-Zn(II) complex catalytic system for the asymmetric Diels-Alder reaction of Brassard-type diene with methyleneindolines was developed. The optically pure spiro[cyclohex[3]ene-1,3'-indoline]-1'-carboxylate-2, 2'-dione derivatives containing three stereocenters were obtained in moderate yields with 98% to >99% ee in a stereospecific manner.
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.
Jianfeng
J
Zheng
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.
Lili
L
Lin
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.
Kai
K
Fu
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.
Haifeng
H
Zheng
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.|Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 300072, P. R. China.
Xiaoming
X
Feng