Desymmetrization of Cyclohexadienones via Intramolecular Stetter Reaction to Construct Tricyclic Carbocycles

Abstract

N-Heterocyclic carbene catalyzed desymmetrization of cyclohexadienones to construct tricyclic carbocycles via an intramolecular enantioselective Stetter reaction was realized. With 10 mol% of d-camphor-derived triazolium salt E and 10 mol% of KOAc, various substituted tricyclic carbocycles bearing a quaternary carbon stereogenic center and two contiguous stereocenters were obtained in excellent yields with up to 89% ee.

Key words

camphor - desymmetrization - N-heterocyclic carbene - organocatalysis - Stetter reaction

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