title: Asymmetric homologation of ketones. A new entry to orthogonally protected (2R,4R)-piperidine-2,4-dicarboxylic acid.
abstract: A new conformationally constrained analogue of glutamic acid has been synthesized efficiently in seven steps from a chiral 2-alkyl-4-piperidone. The synthesis is based on (a) the unprecedented asymmetric one-carbon homologation of the ketone controlled by the size of the N-substituent and (b) the appropriate manipulation of substituents at positions 2 and 4 of the piperidine ring, a step that involves two independent oxidation processes.
authors.affiliation: Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain.
authors.forename: Pablo
authors.initials: P
authors.lastname: Etayo
authors.forename: Ramón
authors.initials: R
authors.lastname: Badorrey
authors.forename: María D
authors.initials: MD
authors.lastname: Díaz-de-Villegas
authors.forename: José A
authors.initials: JA
authors.lastname: Gálvez
mesh_terms: D018698:Glutamic Acid / Q000031:analogs & derivatives; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D010875:Pipecolic Acids / Q000138:chemical synthesis*; D010881:Piperidones / Q000737:chemistry
chemical_list: D007659:Ketones; D010875:Pipecolic Acids; D010881:Piperidones; D018698:Glutamic Acid; C041091:2,4-piperidinedicarboxylic acid