Reactivite comparee des isomeres imine et enamine silicies: Synthese enantioselective de l'(oxo-2 cyclohexyl)-3 propionate de methyle
作者:Michel Fourtinon、Bernard De Jeso、Jean-Claude Pommier
DOI:10.1016/0022-328x(85)87401-5
日期:1985.7
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.
森达之间的异构化方法3 -取代的烯胺和亚胺(Ñ ⇌ Ç -Si)是如此之慢,每个异构体能够独立地反应。硅取代的(S)-苯乙胺衍生物加成丙烯酸甲酯,并在水解时形成(S)-3-(2-氧代环己基)丙烷甲酸甲酯。互变异构亚胺产生(R)-对映异构体。令人惊讶地,在路易斯酸的存在下,含环的有机硅取代的衍生物显示出比相应的锡化合物低的立体选择性。