BASE-INDUCED C-5 EPIMERIZATION OF 4-METHYL-5-PHENYL OXAZOLIDINONES - CHIRAL AUXILIARIES DERIVED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE

Authors
DAVIES SG DOISNEAU GJM
Citation
Sg. Davies et Gjm. Doisneau, BASE-INDUCED C-5 EPIMERIZATION OF 4-METHYL-5-PHENYL OXAZOLIDINONES - CHIRAL AUXILIARIES DERIVED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE, Tetrahedron : asymmetry, 4(12), 1993, pp. 2513-2516
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
12
Year of publication
1993
Pages
2513 - 2516
Database
ISI
SICI code
0957-4166(1993)4:12<2513:BCEO4O>2.0.ZU;2-K
Abstract
Treatment of cis- and trans-4-methyl-5-phenyl oxazolidinones 2 and 3 w ith excess butyllithium at 0 degrees C results in C-5 epimerisation, v ia a common intermediate N,C-5-dianion, generating after protonation a 1:4 mixture of 2:3.