Highly Enantioselective Hydrosilylation of Aromatic Alkenes

Jakob F. Jensen, Bo Y. Svendsen, Thomas V. la Cour, Henriette L. Pedersen, and Mogens Johannsen*
Department of Chemistry, Technical University of Denmark, Building 201, DK-2800 Kgs Lyngby, Denmark
J. Am. Chem. Soc., 2002, 124 (17), pp 4558–4559
DOI: 10.1021/ja025617q
Publication Date (Web): April 4, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  mj@kemi.dtu.dk.

Abstract

Abstract Image

Currently, the most effective and economic way to convert an alkene into an optically active alcohol is the two-step sequence:  hydrosilylation/oxidation. Much work has been devoted to elucidating effective catalysts for this process, but hitherto only one effective and highly stereoselective process has been available. Herein we present a novel catalytic system for the asymmetric hydrosilylation of aromatic alkenes, giving the products in high yields and with the highest enantioselectivity (up to 99% ee) ever observed for this reaction. The reaction works efficiently for a variety of substituted aromatic alkenes, giving access after Tamao oxidation to almost optically pure benzylic alcohols in high yields.

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History

  • Published In Issue May 01, 2002
  • Received January 16, 2002

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