Imine allylation by allylic trimethylsilanes via in situ formation of N-tosyliminium species from carbonyl compounds and toluene-p-sulfonamide with SnCl2 and N-chlorosuccinimide: regioselection and diastereoselection

Abstract

N-Tosyliminium species, prepared in situ from carbonyl compounds and TsNH₂ with SnCl₂ and N-chlorosuccinimide, undergo nucleophilic addition of allylic silanes (imine allylation) to produce the corresponding homoallylic amines; the imine allylation by but-2-enyltrimethylsilane with aldehydes and TsNH₂ leads to regio- and diastereo-selection to produce anti 1-substituted 2-methylbut-3-enylamines.