DIASTEREOSELECTIVE BROMODIFLUOROMETHYLATION AND DIFLUOROMETHYLATION OF CHIRAL IMIDE ENOLATES VIA INSERTION OF DIFLUOROCARBENE

Authors
ISEKI K ASADA D TAKAHASHI M NAGAI T KOBAYASHI Y
Citation
K. Iseki et al., DIASTEREOSELECTIVE BROMODIFLUOROMETHYLATION AND DIFLUOROMETHYLATION OF CHIRAL IMIDE ENOLATES VIA INSERTION OF DIFLUOROCARBENE, Tetrahedron : asymmetry, 7(4), 1996, pp. 1205-1215
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
4
Year of publication
1996
Pages
1205 - 1215
Database
ISI
SICI code
0957-4166(1996)7:4<1205:DBADO>2.0.ZU;2-J
Abstract
Lithium enolates of chiral N-acyloxazolidinones reacted with dibromodi fluoromethane and bromodifluoromethane to give alpha-bromodifluorometh yl and alpha-difluoromethyl carboximides, respectively, with good dias tereomeric excess. These reactions proceed not via a radical mechanism but via an ionic chain mechanism involving insertion of difluorocarbe ne. Copyright (C) 1996 Elsevier Science Ltd