A trans-stereoselective synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones

E Bandini; G Favi; G Martelli; M Panunzio; G Piersanti

doi:10.1021/ol005633x

A trans-stereoselective synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones

Org Lett. 2000 Apr 20;2(8):1077-9. doi: 10.1021/ol005633x.

Authors

E Bandini¹, G Favi, G Martelli, M Panunzio, G Piersanti

Affiliation

¹ ICoCEA-CNR Via Gobetti 101, Bologna, Italy.

PMID: 10804558
DOI: 10.1021/ol005633x

Abstract

[formula: see text] Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting beta-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidinones, valuable intermediates in the synthesis of biologically active compounds.