Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama–Mannich addition

Abstract

A new method for amino acid homologation by way of formal C–C bond functionalization is reported. This method utilizes a 2-step/1-pot protocol to convert α-amino acids to their corresponding N-protected β-amino esters through quinone-catalyzed oxidative decarboxylation/in situ Mukaiyama–Mannich addition. The scope and limitations of this chemistry are presented. This methodology provides an alternative to the classical Arndt–Eistert homologation for accessing β-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.