Open AccessNovel Chiral Thiourea Derived from Hydroquinine and l -Phenylglycinol: An Effective Catalyst for Enantio- and Diastereoselective Aza-Henry Reaction
Author(s) -
Jingdong Wang,
Yuxin Liu,
Zhonglin Wei,
Jungang Cao,
Dapeng Liang,
Yingjie Lin,
Haifeng Duan
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.0c06233
Subject(s) - thiourea , catalysis , nitroaldol reaction , chemistry , isatin , enantioselective synthesis , organocatalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry
A series of chiral thiourea bearing multiple H-bond donors derived from hydroquinine has been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitroalkanes catalyzed by these chiral thioureas can achieve high enantioselectivity (78-99% ee) and excellent diastereoselectivity (up to 99:1). This work is the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.