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

Org Lett. 2005 Sep 1;7(18):3981-4.

PMID: 16119947

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]

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP74830301	Tetrabutylammonium succinimide		74830-30-1	Price