title: 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.
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Haugeberg
authors.affiliation: Eli Lilly and Company, 893 S. Delaware Street, DC - 1920, Indianapolis, IN 46285, USA.
authors.forename: Johnny H
authors.initials: JH
authors.lastname: Phan
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu.
authors.forename: Xinyun
authors.initials: X
authors.lastname: Liu
authors.affiliation: Department of Chemistry, University of California - Berkeley, 419 Latimer Hall, CA 94720-1460, USA.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: O'Connor
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu.
authors.forename: Michael D
authors.identifier: http://orcid.org/0000-0001-6441-9802
authors.initials: MD
authors.lastname: Clift
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000588:Amines; D000596:Amino Acids; D016227:Benzoquinones; C004532:quinone