title: Three component coupling of alpha-iminoesters via umpolung addition of organometals: synthesis of alpha,alpha-disubstituted alpha-amino acids.
abstract: The synthesis of alpha,alpha-disubstituted alpha-amino acids by means of a three component coupling is reported. The coupling occurs through umpolung addition of organometallic reagents to the nitrogen of alpha-iminoesters. The resulting enolate intermediates subsequently react with electrophiles (aldehydes, imines, alpha,beta-unsaturated nitro, alkyl halides, acyl cyanides) to form a quaternary center. Tethering of the electrophile and nucleophile components provides cyclic alpha,alpha-disubstituted alpha-amino acid derivatives.
authors.affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Dickstein
authors.forename: Michael W
authors.initials: MW
authors.lastname: Fennie
authors.forename: Amber L
authors.initials: AL
authors.lastname: Norman
authors.forename: Betty J
authors.initials: BJ
authors.lastname: Paulose
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004952:Esters; D007097:Imines; D009942:Organometallic Compounds