Preparation of azetidines by 4-endo trig cyclizations of N-cinnamyl tosylamides

Authors
Robin, S Rousseau, G
Citation
S. Robin et G. Rousseau, Preparation of azetidines by 4-endo trig cyclizations of N-cinnamyl tosylamides, EUR J ORG C, (17), 2000, pp. 3007-3011
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
17
Year of publication
2000
Pages
3007 - 3011
Database
ISI
SICI code
1434-193X(200009):17<3007:POAB4T>2.0.ZU;2-G
Abstract
Formation of azetidines by electrophilic cyclizations have been reported, s tarting with homoallylic amines (4-exo mode cyclizations). We reported that the formation of these compounds can be carried out starting with allylic amines (4-endo mode cyclizations) using bis(collidine)bromonium(I) hexafluo rophosphate as an electrophile. These cyclizations occur via a carbocation intermediate.