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Preparation of Azetidines by 4‐ endo trig Cyclizations of N ‐Cinnamyl Tosylamides
Author(s) -
Robin Sylvie,
Rousseau Gérard
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3007::aid-ejoc3007>3.0.co;2-e
Subject(s) - chemistry , allylic rearrangement , electrophile , carbocation , hexafluorophosphate , organic chemistry , stereoselectivity , medicinal chemistry , stereochemistry , ionic liquid , catalysis
Formation of azetidines by electrophilic cyclizations have been reported, starting 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) hexafluorophosphate as an electrophile. These cyclizations occur via a carbocation intermediate.