Effective 1,5-Asymmetric Induction in Tin(IV) Chloride Promoted Reactions Between Aldehydes and (4-Alkoxy-2-alkenyl)tributylstannanes
- 1 January 1994
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1994 (03) , 322-334
- https://doi.org/10.1055/s-1994-25469
Abstract
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.Keywords
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