Stereoselectivity in amidyl radical cyclisations: Alkyl mode cyclisations

Authors
Clark, AJ Deeth, RJ Samuel, CJ Wongtap, H
Citation
Aj. Clark et al., Stereoselectivity in amidyl radical cyclisations: Alkyl mode cyclisations, SYNLETT, (4), 1999, pp. 444-446
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
4
Year of publication
1999
Pages
444 - 446
Database
ISI
SICI code
0936-5214(199904):4<444:SIARCA>2.0.ZU;2-B
Abstract
Amidyl radicals 2 generated from tributylstannane mediated homolysis of O-b enzoyl hydroxamic acid derivatives 6a-g undergo alkyl mode 5-exo cyclisatio n to give mixtures of cis and trans N-acyl pyrrolidinones (d.e. = 54-74%). The efficiency of the process was found to be dependant upon the steric and electronic nature of the nitrogen substituent.