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- W2920791159 abstract "Chiral tertiary alcohols are important building blocks for the synthesis of pharmaceutical agents and biologically active natural products. The addition of carbon nucleophiles to ketones is the most common approach to tertiary alcohol synthesis but traditionally relies on stoichiometric organometallic reagents that are difficult to prepare, sensitive, and uneconomical. We describe a mild and efficient method for the copper-catalyzed allylation of ketones using widely available 1,3-dienes as allylmetal surrogates. Homoallylic alcohols bearing a wide range of functional groups are obtained in high yield and with good regio-, diastereo-, and enantioselectivity. Mechanistic investigations using density functional theory (DFT) implicate the in situ formation of a rapidly equilibrating mixture of isomeric copper(I) allyl complexes, from which Curtin–Hammett kinetics determine the major isomer of the product. A stereochemical model is provided to explain the high diastereo- and enantioselectivity of this process. Finally, this method was applied to the preparation of an important drug, (R)-procyclidine, and a key intermediate in the synthesis of several pharmaceuticals." @default.
- W2920791159 created "2019-03-11" @default.
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- W2920791159 date "2019-02-28" @default.
- W2920791159 modified "2023-10-14" @default.
- W2920791159 title "CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications" @default.
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- W2920791159 doi "https://doi.org/10.1021/jacs.9b01784" @default.
- W2920791159 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6572726" @default.
- W2920791159 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30817137" @default.
- W2920791159 hasPublicationYear "2019" @default.
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