title: The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
abstract: Optically active (S)-alpha-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-alpha-amino acids are available in 59-92% ee (3 cases) by using cinchonine as the chiral control element.
authors.affiliation: Department of Chemistry, Indiana University Purdue University Indianapolis, 46202, USA. odonnell@chem.iupui.edu
authors.forename: Martin J
authors.initials: MJ
authors.lastname: O'Donnell
authors.forename: Mark D
authors.initials: MD
authors.lastname: Drew
authors.forename: Jeremy T
authors.initials: JT
authors.lastname: Cooper
authors.forename: Francisca
authors.initials: F
authors.lastname: Delgado
authors.forename: Changyou
authors.initials: C
authors.lastname: Zhou
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001880:Boranes; D009942:Organometallic Compounds