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. 2017 Mar 9;53(21):3062-3065.
doi: 10.1039/c7cc00485k.

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

Benjamin J Haugeberg  1 , Johnny H Phan  2 , Xinyun Liu  1 , Thomas J O'Connor  3 , Michael D Clift  1
Affiliations

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

Benjamin J Haugeberg et al. Chem Commun (Camb). .

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.

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Figures

Figure 1
Figure 1
β-Amino Acid Derivatives in FDA-Approved Therapeutics.
Scheme 1
Scheme 1
Classical Amino Acid Homologation and This Work.
Scheme 2
Scheme 2
Proposed Method for Quinone-Catalyzed Amino Acid Homologation.
See this image and copyright information in PMC

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