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Synthesis 1994; 1994(3): 322-334
DOI: 10.1055/s-1994-25469
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Effective 1,5-Asymmetric Induction in Tin(IV) Chloride Promoted Reactions Between Aldehydes and (4-Alkoxy-2-alkenyl)tributylstannanes

Alan H. Mcneill* , Eric J. Thomas
  • *Department of Chemistry, The University of Manchester, Manchester M13 9PL, England
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Publication Date:
27 September 2002 (online)

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Transmetallation of (S)-4-benzyloxy-2-pentenyl(tributyl)stannane (1) using tin(IV) chloride generates an allyltin trichloride which reacts in situ with aldehydes to give 1-substituted syn-(3Z)-5-benzyloxyhexenols with excellent stereoselectivity. With chiral aldehydes, the stereoselectivity of the reaction is dominated by the reagent, except for 2-alkoxyaldehydes which show matching and mismatching consistent with preferred Felkin-Anh diastereofacial selectivity.

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