Induction asymétrique—IV: Etude des modes de reconnaissance intermoléculaire des β-aminocétones aromatiques prochirales,par les réactifs de réformatsky. Mise en évidence d'un phénoméne de participation |
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| Authors: | Marc Lucas Jean Paul Guetté |
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| Institution: | Laboratoire de Chimie Organique des Hormones, Collége de France, 11, place Marcelin Berthelot, 75231 Paris Cedex 05, France;Laboratoire de Chimie Organique en vue des Applications, Conservatoire National des Arts et Métiers, 292 rue Saint-Martin, 75141 Paris Cedex 03, France |
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| Abstract: | In the reaction of Reformatsky reagents (R-CHZnBr-CO2R') with aromatic β-aminoketones (C6H5-CO-CH2-CH2-NR″2, mixtures of erythro and threo diastereomeric amino-hydroxyesters, with the former predominating, were obtained.The proposed bicyclic transition states involve the participation of the neighbouring nitrogen atom, and support the direction and the magnitude of the observed asymmetric induction. The relative stabilities of diastereomeric transition states are discussed in terms of steric and electronic effects. |
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