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Direct Catalytic Enantioselective Reduction of Achiral α,β-Ynones. Strong Remote Steric Effects Across the C−C Triple Bond

Helal, Christopher J. ; Magriotis, Plato A. ; Corey, E. J.

Journal of the American Chemical Society, 01/1996, Vol.118(44), pp.10938-10939 [Peer Reviewed Journal]

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  • Title:
    Direct Catalytic Enantioselective Reduction of Achiral α,β-Ynones. Strong Remote Steric Effects Across the C−C Triple Bond
  • Author: Helal, Christopher J. ; Magriotis, Plato A. ; Corey, E. J.
  • Description: The first catalytic enantioselective reduction of alpha,beta-ynones, a direct and highly effective approach, is described. The reaction provides useful propargylic alcohols of very high optical purity in excellent yields. High enantioselectivity with oxazaborolidine is attributed to a remarkable remote steric effect across the C-C bond. It involves the distal i-Pr3Si substituent of the substrate and the Me3SiCH2 group on the boron atom of oxazaborolidine, which compellingly rejects the minor pathway.
  • Is Part Of: Journal of the American Chemical Society, 01/1996, Vol.118(44), pp.10938-10939
  • Identifier: ISSN: 0002-7863 ; E-ISSN: 1520-5126 ; DOI: http://dx.doi.org/10.1021/ja962849e
  • Subjects: Oxidation-reduction Reactions -- Research ; Alcohols -- Analysis ; Organic Compound Synthesis
  • Language: English
  • Source: American Chemical Society (via CrossRef)

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