MN(III)-PROMOTED SULFUR-DIRECTED 4-EXO-TRIG RADICAL CYCLIZATION OF ENAMIDES TO BETA-LACTAMS

Authors
ATTENNI B CERRETI A DANNIBALE A RESTA S TROGOLO C
Citation
B. Attenni et al., MN(III)-PROMOTED SULFUR-DIRECTED 4-EXO-TRIG RADICAL CYCLIZATION OF ENAMIDES TO BETA-LACTAMS, Tetrahedron, 54(39), 1998, pp. 12029-12038
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
39
Year of publication
1998
Pages
12029 - 12038
Database
ISI
SICI code
0040-4020(1998)54:39<12029:MS4RCO>2.0.ZU;2-1
Abstract
The synthesis of beta-lactams vinylated at C-4 from N-(3-phenylthio-1- alkenyl)amides was carried out by Mn(III)-promoted 4-exo-trig radical cyclization followed by beta-fragmentative loss of phenylthiyl radical . The effects on the reaction course of different substituents both on enamidic nitrogen atom or double bond were analyzed. The overall reac tion was stereoselective, leading to trans azetidinones. (C) 1998 Publ ished by Elsevier Science Ltd. All rights reserved.