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 ß-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 ß-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.
Subject(s)
Amines/chemical synthesis , Amino Acids/chemistry , Benzoquinones/chemistry , Amines/chemistry , Catalysis , Decarboxylation , Molecular Structure , Oxidation-ReductionABSTRACT
A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage.
