Highly enantioselective alpha-chlorination of cyclic beta-ketoesters catalyzed by N,N'-dioxide using NCS as the chlorine source.
A simple and highly efficient N,N'-dioxide organocatalyst system was developed for the asymmetric alpha-chlorination of cyclic beta-ketoesters using easily available NCS as the chlorine source to provide a series of optically active alpha-chloro-beta-ketoesters in excellent yields with 90-98% ee.
Cai
Yunfei
Y
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Wang
Wentao
W
Shen
Ke
K
Wang
Jun
J
Hu
Xiaolei
X
Lin
Lili
L
Liu
Xiaohua
X
Feng
Xiaoming
X
D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D007659:Ketones; D002713:Chlorine