Organocatalytic ring expansion of beta-lactams to gamma-lactams through a novel N1-C4 bond cleavage. direct synthesis of enantiopure succinimide derivatives

Benito Alcaide; Pedro Almendros; Gema Cabrero; M Pilar Ruiz

doi:10.1021/ol051504a

Organocatalytic ring expansion of beta-lactams to gamma-lactams through a novel N1-C4 bond cleavage. direct synthesis of enantiopure succinimide derivatives

Org Lett. 2005 Sep 1;7(18):3981-4. doi: 10.1021/ol051504a.

Authors

Benito Alcaide¹, Pedro Almendros, Gema Cabrero, M Pilar Ruiz

Affiliation

¹ Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es

PMID: 16119947
DOI: 10.1021/ol051504a

Abstract

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]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Lactams / chemistry*
Molecular Structure
Stereoisomerism
Succinimides / chemical synthesis*
Succinimides / chemistry

Substances

Lactams
Succinimides