The preparation of vinylstannanes via the Peterson reaction

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

“…The first is when the “anion” is stabilized, as it is to some extent by the presence of another metal group. Carbon nucleophiles carrying both an α-silyl group and another α-metal show high chemoselectivity for silyl removal over that of the other metal, and vinylboron, vinylselenium, vinyltin, and vinyllead compounds can be made this way, usually with fairly low levels of stereoselectivity in favor of the Z isomer. When the nucleophile has two α-silyl groups, creating an intermediate 18 with diastereotopic silyl groups, the one removed, normally, but not always, is that which leads to a trans double bond 19 (Scheme ). , When there is another substituent, as with the bromide 20 , the elimination is not highly stereoselective, giving the ( E )- and ( Z )-vinylsilanes 21 and 22 in equal amounts …”