General approach for the stereocontrolled construction of the beta-lactam ring in amino acid-derived 4-alkyl-4-carboxy-2-azetidinones.
The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N(alpha)-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).
Gerona-Navarro
Guillermo
G
Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. iqmg313@iqm.csic.es
García-López
M Teresa
MT
González-Muñiz
Rosario
R
D000596:Amino Acids / Q000737:chemistry*; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
C116379:2-azetidinone; D000596:Amino Acids; D001384:Azetidines; D004151:Dipeptides; D047090:beta-Lactams