HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TITANIUM ENOLATE OF A CHIRAL 2-PYRIDYLTHIOESTER WITH CHIRAL IMINES

Authors
ANNUNZIATA R BENAGLIA M CHIOVATO A CINQUINI M COZZI F
Citation
R. Annunziata et al., HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TITANIUM ENOLATE OF A CHIRAL 2-PYRIDYLTHIOESTER WITH CHIRAL IMINES, Tetrahedron, 51(36), 1995, pp. 10025-10032
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
36
Year of publication
1995
Pages
10025 - 10032
Database
ISI
SICI code
0040-4020(1995)51:36<10025:HSSOBB>2.0.ZU;2-J
Abstract
The reaction of the titanium enolate of a 2-pyridylthioester derived f rom (R)-3-hydroxybutyric acid with chiral imines affords 3,3'-anti-3,4 -trans configurated beta-lactams in a highly selective fashion. The me thodology has been applied to the synthesis of a precursor of the carb apenem antibiotic 1 beta-methylthienamycin.