Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines.
An organocatalyzed direct asymmetric vinylogous Michael addition reaction of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines has been developed with a chiral bifunctional amine-squaramide as the catalyst. This approach provides easy access to a series of optically active α,β-unsaturated γ-substituted butyrolactams in high yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1) and enantioselectivities (up to >99% ee).
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Zhen-Hua
ZH
Wang
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
Zhi-Jun
ZJ
Wu
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Deng-Feng
DF
Yue
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Yong
Y
You
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn.
Xiao-Ying
XY
Xu
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn.
Xiao-Mei
XM
Zhang
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn.
Wei-Cheng
WC
Yuan