Facile generation of [bis(2-pyridyldimethylsilyl)methyl]lithium and its reaction with carbonyl compounds. New method for the stereoselective synthesis of vinylsilanes

Article abstract of DOI:10.1016/S0040-4020(01)00348-9

The generation of (2-PyMe₂Si)₂CHLi was easily accomplished by the deprotonation of (2-PyMe₂Si)₂CH₂ using n-BuLi in Et₂O. The ¹H NMR analysis of (2-PyMe₂Si)₂CHLi in Et₂O-d₁₀ revealed the coordination of both pyridyl groups to lithium. Thus generated (2-PyMe₂Si)₂CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities (>99% E).