Synlett 1989; 1989(1): 59-62
DOI: 10.1055/s-1989-34711
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Asymmetric Synthesis of α-Substituted Benzyl Alcohols via the Stereoselective Addition of Nucleophiles to Homochiral Tricarbonyl (η6-o-triisopropylsilylbenzaldehyde)chromium(0)

Stephen G. Davies* , Craig L. Goodfellow
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, England
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Publication History

Publication Date:
26 February 2002 (online)

The addition of nucleophiles to homochiral tricarbonyl-(η6-ο-triisopropylsilylbenzaldehyde)chromium(0) proceeds with complementary diastereoselectivities in the presence or absence of strong Lewis acidic species. Fluoride-mediated desilylation of each diastereoisomer followed by oxidative decomplexation yields α-substituted benzyl alcohols in high enantiomeric excesses.