A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines.
An efficient self-assembled methanoproline-thiourea organocatalyst for the synthesis of optically active 6-isopropyl-3,4-dihydro-pyrimidines via an asymmetric Biginelli reaction was developed, which is superior to the individual precatalyst. A wide range of optically active 6-isopropyl-3,4-dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with excellent enantioselectivities (up to 99% ee). A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com.
Zhijun
Z
Hang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com.
Jun
J
Zhu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com.
Xiang
X
Lian
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com.
Peng
P
Xu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com and Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Han
H
Yu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. hanyu201212@gmail.com hansheng654321@sina.com.
Sheng
S
Han