On the Lewis acid-catalysed reaction of the 2,3-bis(trimethylstannyl)-1-alkene moiety with aldehydes

Article abstract of DOI:10.1016/0022-328X(91)86010-N

Compounds containing the 2,3-bis(trimethylstannyl)-1-alkene moiety react with aldehydes in the presence of boron trifluoride etherate to give homoallylic alcohols in which the remaining vinylic stannyl moiety has undergone halodemethylation.A mechanistic explanation for this behaviour is presented.NMR studies indicate that the addition proceeds in an erythro-selective manner.