This paper is concerned with the asymmetric synthesis of 2-alkylcyclohexanones (VI) by alkylation of cyclohexanone enamines (III) of L-proline ester derivatives. Acrylonitrile, methyl acrylate, allyl bromide and ethyl bromoacetate were used as alkylating agents. Several reaction conditions were examined, and plausible reaction mechanisms were proposed. Rates of racemization for VIa and -Vic were determined.
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Hiroi et al. (1972) studied this question.