Tetrahedron p. 1371 - 1380 (1984)
Update date:2022-08-04
Topics:
Midland, M. Mark
Tramontano, Alfonso
Kazubski, Aleksander
Graham, Richard S.
Tsai, David J. S.
Cardin, Daniel B.
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 ca be prepared from the reagent derived from 9-BBn and the benzyl ether of nopol (6,6-dimethyl-bicyclo<3.1.1>hept-2-ene-2-ethanol).The limiting factor in obtaining high enantiomeric induction is often the enantiomeric purity of the α-pinene.With 100percent enantiomerically pure α-pinene, propargyl alcohols of essentially 100percent 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.
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Doi:10.1021/jo00177a032
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