Aldehydes α-silyles: preparation et properties nouvelles

Article abstract of DOI:10.1016/0022-328X(89)88060-X

t-Butyldimethylsilyl acetaldehyde (3) is obtained from the hydrolysis of the (Z)-β-silylenoxysilane (2), prepared from (Z)-1-bromo-2-(trimethylsiloxy)ethylene by reaction with t-butyllithium followed by condensation with t-butyldimethylsilyl triflate.The lithium enolate of aldehyde 3 is prepared direct by reaction with lithium diisopropylamide or lithium hexamethyldisilazane; its condensation with trimethylchlorosilane leads to the (E)-β-silylenoxysilane (2) and with aldehydes, to α,β-ethylenic aldehydes (4).