Organic Letters 2013-03-15

Squaramide-tertiary amine catalyzed asymmetric cascade sulfa-Michael/Michael addition via dynamic kinetic resolution: access to highly functionalized chromans with three contiguous stereocenters.

Wen Yang, Yi Yang, Da-Ming Du

Index: Org. Lett. 15(6) , 1190-3, (2013)

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Abstract

An efficient asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa-Michael/sulfa-Michael/Michael reaction process, involving dynamic kinetic resolution, is described.