Affiliation:
1. College of Pharmacy, Guangxi Zhuang Yao Medicine Center of Engineering and Technology, Guangxi University of Chinese Medicine
2. Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University
Abstract
Under bifunctional squaramide and thiourea organocatalysis, a series of vicinally bis(trifluoromethyl)-substituted 3,3′-pyrrolidinyl spirooxindoles were successfully synthesized via 1,3-dipolar cycloaddition reactions of 3-(trifluoroethylidene)oxindoles with diethyl 2-((2,2,2-trifluoroethyl)imino)malonate and N-(2,2,2-trifluoroethyl)isatin ketimines. The highlight of this protocol is the efficient construction of the vicinally bis(trifluoromethyl)-substituted pyrrolidine unit of spirooxindoles, including multiple contiguous stereogenic centres, in excellent yields and stereoselectivities.
Funder
National Natural Science Foundation of China
Natural Science Foundation of Guangxi Province
Guangxi University of Chinese Medicine
Subject
Organic Chemistry,Catalysis
Cited by
21 articles.
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