REACTIVITE COMPAREE DES ISOMERES IMINE ET ENAMINE SILICIES: SYNTHESE ENANTIOSELECTIVE DE L'(OXO-2 CYCLOHEXYL)-3 PROPIONATE DE METHYLE

Article abstract of DOI:10.1016/0022-328X(85)87401-5

The isomerisation process between SiMe3-substituted enamines and imines (N-Si<*>C-Si) is so slow that each isomer is able to react independently.The silicon-substituted (S)-phenylethylamine derivative adds to methyl acrylate and forms, upon hydrolysis, methyl (S)-3-(2-oxocyclohexyl)propane carboxylate.The tautomeric imine leads to the (R)-enantiomer.Surprisingly, in the presence of a Lewis acid, the ring-containing organosilicon-substituted derivatives show lower stereoselectivity than the corresponding tin compounds.