Effective 1,5-asymmetric induction in tin(IV) chloride promoted reactions between aldehydes and (4-alkoxy-2-alkenyl)tributylstannanes

Article abstract of DOI:10.1055/s-1994-25469

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.