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- W1525054489 abstract "Propargyl ketones are readily reduced by the asymmetric reducing agent B-3-pinanyl-9- borabicyclo[3.3.1]-nonane (Alpine-borane). The reagent prepared from (+)-α-pinene and 9-BBN provides the R enantiomer while the S enantiomer can be obtained from (-)-α-pinene. Alternatively the S enantiomer can be prepared from the reagent derived from 9-BBN and the benzyl ether of nopol (6,6-dimethyl-bicyclo[3.11.]hept-2-ene-2-ethanol). The limiting factor in obtaining high enantiomeric induction is often the enantiomeric purity of the α-pinene. With 100% enantiomerically pure α-pinene, propargyl alcohols of essentially 100% ee can be obtained. A predictive rationalization of the transition state leading to this remarkable selection is presented. The acetylene unit of the propargyl alcohol provides a convenient handle for transformations to other useful, optically-active products. The use of propargyl alcohols for the synthesis of optically-active α- and β-substituted γ-lactones, and δ-lactones is illustrated" @default.
- W1525054489 created "2016-06-24" @default.
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- W1525054489 date "1984-01-01" @default.
- W1525054489 modified "2023-10-02" @default.
- W1525054489 title "Asymmetric reductions of propargyl ketones" @default.
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- W1525054489 doi "https://doi.org/10.1016/s0040-4020(01)82422-4" @default.
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