Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods

Authors
Davies, DT Kapur, N Parsons, AF
Citation
Dt. Davies et al., Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods, TETRAHEDRON, 56(24), 2000, pp. 3941-3949
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
24
Year of publication
2000
Pages
3941 - 3949
Database
ISI
SICI code
0040-4020(20000609)56:24<3941:PONBRC>2.0.ZU;2-8
Abstract
Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipy ridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) re actions were generally more problematic, giving related dienes in lower yie ld (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.