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

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.

Automated summary

In this study, we presented an efficient strategy for the enantioselective synthesis of 2,3-furan-fused carbocycles with three contiguous stereocenters. This transformation is catalyzed by PtCl4/chiral amines through tandem dehydrogenative annulation/Diels-Alder reaction of 2-(1-alkynyl)-2-alken-1-ones and enals, with in situ generation of furan-based ortho-quinodimethane intermediates and iminium activation of enals being crucial to the process.