A novel one-step approach for the preparation of alpha-amino acids, alpha-amino amides, and dipeptides from azetidine-2,3-diones.
A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of alpha-amino acids, alpha-amino amides, and dipeptides, was developed in both the racemic and optically pure forms. The current mechanistic hypothesis invokes a concerted process involving CO extrusion. However, a stepwise pathway can also account for these novel transformations.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Aragoncillo
Cristina
C
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014867:Water / Q000737:chemistry
D000588:Amines; D000596:Amino Acids; D001384:Azetidines; D004151:Dipeptides; D014867:Water