The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(i) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations. This journal is
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Zhang, L. (Contributor), Yamazaki, K. (Contributor), Leitch, J. A. (Contributor), Manzano, R. (Contributor), Atkinson, V. A. M. (Contributor), Hamlin, T. A. (Contributor) & Dixon, D. J. (Contributor), Unknown Publisher, 28 Jun 2020