Ir-catalyzed chemo- and enantioselective hydrogenation of enyne-conjugated ketones

The asymmetric hydrogenation of beta-alkynyl alpha,beta-unsaturated ketones has been achieved by using Ir/f-phamidol as a catalyst under mild conditions, providing the corresponding chiral alcohols in high yields (up to 99% yield) and with excellent enantioselectivities (up to 99% ee). Moreover, the reaction performed well on a gram scale with 0.1 mol% catalytic loading, indicating the potential use of this protocol in the synthesis of chiral alkyl alcohols, drugs and natural products. We herein report an efficient asymmetric hydrogenation of beta-alkynyl alpha,beta-unsaturated ketones by using Ir/f-phamidol as a catalyst under mild conditions, providing the corresponding chiral alcohols in up to 99% yield and 99% ee.