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Highly enantioselective tandem cycloisomerization/Diels–Alder reaction of 2-(1-alkynyl)-2-alken-1-ones and enals: dual catalysis with platinum and amines†
Chemical Communications Pub Date : 05/05/2021 00:00:00 , DOI:10.1039/D1CC02080C
Abstract

Herein, we disclosed a highly efficient strategy of enantioselective synthesis of 2,3-furan-fused carbocycles bearing three-contiguous stereocenters. This transformation is catalyzed by dual catalysis of PtCl4/chiral amines via tandem dehydrogenative annulation/Diels–Alder reaction of 2-(1-alkynyl)-2-alken-1-ones and enals. The in situ generation of the furan-based ortho-quinodimethane intermediates and the iminium activation of enals are crucial to this transformation.

Graphical abstract: Highly enantioselective tandem cycloisomerization/Diels–Alder reaction of 2-(1-alkynyl)-2-alken-1-ones and enals: dual catalysis with platinum and amines
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