New synthetic method of optically active α-methylproline and α-methylpipecolinic acid using electrochemical oxidation as a key reaction

Article abstract of DOI:10.1016/0040-4039(96)01919-3

A new method for the stereoselective α-methylation of N-protected L-proline and L-pipecolinic acid esters is presented. The method consisted of electrochemical α'-methoxylation of the α-amino acid derivatives, the replacement of the α'-methoxy group with a phenylthio group, α-methylation, and reductive removal of the α'-phenylthio group, successively. The intermediates in this method could be used for the preparation of optically active acyclic α-methylated α-amino acids.