Organocatalytic ring expansion of beta-lactams to gamma-lactams through a novel N1-C4 bond cleavage. direct synthesis of enantiopure succinimide derivatives.
Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have also been developed. [reaction: see text]
Alcaide
Benito
B
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Cabrero
Gema
G
Ruiz
M Pilar
MP
D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013388:Succinimides / Q000138:chemical synthesis* / Q000737:chemistry
D007769:Lactams; D013388:Succinimides