Stereochemical aspects in the aminoalkylation reactions of ketones

A simple "one-pot" method has been developed for the amino-methylation of ketones possessing an α-hydrogen under aprotic conditions. The procedure utilises chlorotrimethylsilane in the sequential formation of the intermediate trimethylsilyl enol ether and methylene iminium species. The methylene iminium ion intermediate is generated either from a dialkylaminoalkoxymethane or a bis-(dialkylamino)methane. [Continues.]