The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
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.
O'Donnell
Martin J
MJ
Department of Chemistry, Indiana University Purdue University Indianapolis, 46202, USA. odonnell@chem.iupui.edu
Drew
Mark D
MD
Cooper
Jeremy T
JT
Delgado
Francisca
F
Zhou
Changyou
C
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D001880:Boranes; D009942:Organometallic Compounds