Reactivite comparee des isomeres imine et enamine silicies: Synthese enantioselective de l'(oxo-2 cyclohexyl)-3 propionate de methyle

M Fourtinon, B De Jeso, JC Pommier

Index: Fourtinon, Michel; Jeso, Bernard de; Pommier, Jean-Claude Journal of Organometallic Chemistry, 1985 , vol. 289, p. 239 - 246

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Citation Number: 6

Abstract

Abstract The isomerisation process between SiMe 3-substituted enamines and imines (N⇌ 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 ...