Metallic salt promoted radical cyclization of beta-keto carboxamides and their corresponding beta-enamino carboxamides

Authors
Cossy, J Bouzide, A Leblanc, C
Citation
J. Cossy et al., Metallic salt promoted radical cyclization of beta-keto carboxamides and their corresponding beta-enamino carboxamides, J ORG CHEM, 65(22), 2000, pp. 7257-7265
Citations number
62
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
22
Year of publication
2000
Pages
7257 - 7265
Database
ISI
SICI code
0022-3263(20001103)65:22<7257:MSPRCO>2.0.ZU;2-6
Abstract
Substituted lactams and spirolactams were obtained by Mn(III)-induced radic al cyclization of unsaturated beta -keto carboxamides. Treatment of the cor responding tertiary enamines under similar reaction conditions and in the p resence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines le ads to diastereomeric spirolactams in an approximately 3:1 ratio.