Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles?

Organic Chemistry Frontiers Pub Date: 2017-03-16 DOI: 10.1039/C6QO00852F

Abstract

A highly efficient method for the construction of pyrrolidinyl spirooxindoles with 3-isothiocyanato oxindoles and chalcones via a Michael/cyclization cascade reaction has been developed by using bifunctional cinchona-derived squaramide organocatalysts. A series of complex pyrrolidinyl spirooxindoles could be obtained in high yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >99?:?1 dr, >99% ee) under mild conditions.

Graphical abstract: Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles
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