Phosphine-Catalyzed Cascade [3 + 2] Cyclization−Allylic Alkylation, [2 + 2 + 1] Annulation, and [3 + 2] Cyclization Reactions between Allylic Carbonates and Enones

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Abstract

The phosphine-catalyzed annulations between Morita-Baylis-Hillman adduct carbonates and enones are reported. Under the catalysis of PBu(3) (20 mol %), cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions chemoselectively occur depending on the substituent variation of both the carbonate and enone. These reactions provide efficient syntheses of highly functionalized cyclopentenes and cyclopentanes.

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