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Synlett 1992; 1992(7): 585-586
DOI: 10.1055/s-1992-21424
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Remote Asymmetric Induction in Reactions between Allylstannanes and Aldehydes: Influence of a Homoallyl Ether Substituent in the Stannane

John S. Carey* , Eric J. Thomas
  • *Department of Chemistry, University of Manchester, Manchester M13 9PL, England
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Publication Date:
08 March 2002 (online)

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Transmetallation of (4R)-4-methyl-5-phenylmethoxypent-2-enyl(tributyl)stannane (7) using tin(IV) chloride gives an intermediate which reacts with aldehydes with excellent 1,5-asymmetric induction. For example, benzaldehyde yielded (1S,3Z,5R)-5-methyl-1-phenyl-6-phenylmethoxy-3-hexenol (8) in 86% yield.