Highly Enantioselective Hydrosilylation of Aromatic Alkenes

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 proces...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-05, Vol.124 (17), p.4558-4559
Main Authors: Jensen, Jakob F, Svendsen, Bo Y, la Cour, Thomas V, Pedersen, Henriette L, Johannsen, Mogens
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja025617q