Palladium(ii)-catalyzed enantioselective desymmetrization ring opening of oxabicyclic alkenes with alkynylanilines: efficient access to enantioenriched functionalized cyclohexenes

Abstract

We disclose herein a practical enantioselective desymmetrization ring-opening coupling of oxabicyclic alkenes with alkynylanilines, enabled by Pd(II)-catalyzed aminopalladation cascade, allowing efficient access to a diverse set of indolated cyclohexenes bearing four contiguous densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Representative post-transformations to other valuable enantioenriched functionalized cyclohexene derivatives demonstrate the synthetic potential of this methodology.