Devices for Memory of Chirality in Electrochemical Decarboxylation of alpha-Amino Acid Derivatives

摘要

A replacement of a carboxyl group of N-acylated alpha-amino acids 1 with methoxy group to give a-methoxylated N-acylamino compounds 3 can be easily achieved by electrochemical oxidation of 1 in methanol (eq 1),and the transformation is often used in organic synthesis.However,there has not been any stereochemical studies on this type of reaction except ones concerned with diastereoselectivity.This is possibly due to the preconceived notion that the transformation involves acyliminium ions 2 as the intermediates in which the stereochemistry in 1 might be lost.