REACTIVITE COMPAREE DES ISOMERES IMINE ET ENAMINE SILICIES: SYNTHESE ENANTIOSELECTIVE DE L'(OXO-2 CYCLOHEXYL)-3 PROPIONATE DE METHYLE
The isomerisation process between SiMe3-substituted enamines and imines (N-SiC-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.
Fourtinon, Michel,Jeso, Bernard de,Pommier, Jean-Claude
p. 239 - 246
(2007/10/02)
IMINE SYNTHESIS IN STRICTLY NEUTRAL CONDITIONS
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Stetin, C.,Jeso, B. de,Pommier, J.C.
p. 495 - 500
(2007/10/02)
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