A mild and efficient
telescoped procedure for the stereoselective
alkenylation of simple, non-activated amides using LiCH2SiMe3and carbonyl compounds as surrogates of alkenyllithium
reagents is reported. Our methodology relies on the formation of stable
tetrahedral intermediates, which, upon collapse into highly reactive
lithium enolates in a solvent-dependent fashion, allows for the assembly
of α,β-unsaturated ketones in a single synthetic operation
with high stereoselectivity.