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Homologation of ?-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 ?-amino acids to their corresponding N-protected ?-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 ?-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.

SUBMITTER: Haugeberg BJ

PROVIDER: S-EPMC5604228 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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

Haugeberg Benjamin J BJ Phan Johnny H JH Liu Xinyun X O'Connor Thomas J TJ Clift Michael D MD

Chemical communications (Cambridge, England) 20170301 21

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 result ...[more]

PMID: 28243665

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