Asymmetric Synthesis of Vicinally Bis(trifluoromethyl)-Substituted 3,3′-Pyrrolidinyl Spirooxindoles via Organocatalytic 1,3-Dipolar Cycloaddition Reactions

^§ These two authors contributed equally to this work.

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.

Key words

asymmetric catalysis - azomethine ylides - 1,3-dipolar cyclo­addition­ - bis(trifluoromethyl)-substituted pyrrolidines - bifunctional organocatalysts­

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