Reactivity of (E)-1-(tert-butyldimethyl)silyloxy-3,3-bis(tributylstannyl)propene: Syn selective S(E') addition to aldehydes

Article abstract of DOI:10.1016/S0040-4039(97)01559-1

The reactivity of (E)-1-(tert-butyldimethyl)silyloxy-3,3-bis(tributylstannyl)propene 1 as potential 1,3 dianion equivalent has been investigated. Condensation with aldehydes 4a-h, in presence of BF₃·OEt₂, afforded in high yields the mono-protected diols 5a-h exhibiting an exclusive E configuration of the vinyltin residue. Good to high syn selectivities have been measured, in agreement with an S(E') addition mechanism. Further transformation of the resulting vinyltin moiety of these diols into various functionalities has been successfully tested.