Issue 21, 2017

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
18 Jan 2017
Accepted
13 Feb 2017
First published
13 Feb 2017

Chem. Commun., 2017,53, 3062-3065

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

B. J. Haugeberg, J. H. Phan, X. Liu, T. J. O'Connor and M. D. Clift, Chem. Commun., 2017, 53, 3062 DOI: 10.1039/C7CC00485K

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