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Iridium-Catalyzed Branch-Selective and Enantioselective Hydroalkenylation of α-Olefins through C-H Cleavage of Enamides.

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Catalytic branch-selective hydrofunctionalization of feedstock α-olefins to form enantioenriched chiral compounds is a particularly attractive yet challenging transformation in asymmetric catalysis. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of α-olefins… Click to show full abstract

Catalytic branch-selective hydrofunctionalization of feedstock α-olefins to form enantioenriched chiral compounds is a particularly attractive yet challenging transformation in asymmetric catalysis. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of α-olefins through directed C-H cleavage of enamides. This atom-economical addition process is highly branch-selective and enantioselective, delivering trisubstituted alkenes with an allylic stereocenter. DFT calculations reveal the origin of regio- and enantioselectivity.

Keywords: hydroalkenylation olefins; selective enantioselective; iridium catalyzed; branch selective; cleavage enamides

Journal Title: Journal of the American Chemical Society
Year Published: 2022

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