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

Chem Commun (Camb). 2021 May 13. doi: 10.1039/d1cc02080c. Online ahead of print.ABSTRACTHerein, 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.PMID:33982035 | DOI:10.1039/d1cc02080c

Source: Chemical Communications - May 13, 2021 Category: Chemistry Authors: Liejin Zhou Lu Liu Source Type: research