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Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu−H‐Catalyzed Si−O Coupling
Authors:Jan Seliger  Xichang Dong  Martin Oestreich
Abstract:A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst‐controlled enantioselective silylation. This non‐enzymatic kinetic resolution is catalyzed by a Cu?H species and makes use of the commercially available precatalyst MesCu/(R,R)‐Ph‐BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl‐ as well as dialkyl‐substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post‐functionalization in this position (s up to 207).
Keywords:asymmetric catalysis  copper  dehydrogenative coupling  silicon  tertiary alcohols
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