General and highly efficient synthesis of 2-alkylideneazetidines and beta-lactams via copper-catalyzed intramolecular N-vinylation

Hongjian Lu; Chaozhong Li

doi:10.1021/ol062274i

General and highly efficient synthesis of 2-alkylideneazetidines and beta-lactams via copper-catalyzed intramolecular N-vinylation

Org Lett. 2006 Nov 9;8(23):5365-7. doi: 10.1021/ol062274i.

Authors

Hongjian Lu¹, Chaozhong Li

Affiliation

¹ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PRC.

PMID: 17078719
DOI: 10.1021/ol062274i

Abstract

[Structure: see text] N-Tosyl-3-halo-3-butenylamines underwent efficient Ullmann-type coupling with the catalysis of CuI/N,N'-dimethylethylenediamine to afford 2-alkylideneazetidines, which could be readily converted to the corresponding beta-lactams by oxidation with O3.