SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TIN ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - A COMPARISON BETWEEN TITANIUM AND TIN ENOLATES

Authors
ANNUNZIATA R BENAGLIA M CINQUINI M COZZI F RAIMONDI L
Citation
R. Annunziata et al., SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TIN ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - A COMPARISON BETWEEN TITANIUM AND TIN ENOLATES, Tetrahedron, 50(19), 1994, pp. 5821-5828
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
19
Year of publication
1994
Pages
5821 - 5828
Database
ISI
SICI code
0040-4020(1994)50:19<5821:SOBBCO>2.0.ZU;2-O
Abstract
Addition of tricthylamine to a mixture of 2-pyridylthioesters and SnCl 4 or SnBr4 affords the corresponding tin(IV) enolates that add to imin es to give beta-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.