Réactivité du 3,3-bis(triméthylsilyl)propène vis-à-vis des ions iminium issus d’amines primaires. Accès à des hétérocycles azotés

The 3,3-bis(trimethylsilyl)propene reacts with iminium ions (generated in situ from primary amines) by an aminomethylation–desilylation process and a subsequent cyclization, leading to N-alkyl-1,2,3,6-tetrahydropyridines as principal products. Tetrahydro-1,3-oxazines with a bis(trimethylsilyl)methyl group may also be observed. When primary amines with a tertiary group are used, the reaction leads only to ω-aminovinylsilanes, the steric hindrance inhibiting the progression of the reaction.