RING EXPANSION OF N-ACYL AZIRIDINE-2-IMIDES TO OXAZOLINE-4-IMIDES, USEFUL PRECURSORS OF PURE BETA-HYDROXY ALPHA-AMINO-ACIDS

Authors
CARDILLO G GENTILUCCI L TOLOMELLI A TOMASINI C
Citation
G. Cardillo et al., RING EXPANSION OF N-ACYL AZIRIDINE-2-IMIDES TO OXAZOLINE-4-IMIDES, USEFUL PRECURSORS OF PURE BETA-HYDROXY ALPHA-AMINO-ACIDS, Tetrahedron letters, 38(39), 1997, pp. 6953-6956
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
39
Year of publication
1997
Pages
6953 - 6956
Database
ISI
SICI code
0040-4039(1997)38:39<6953:REONAT>2.0.ZU;2-R
Abstract
Optically active N-acyl aziridine P-imides or 2-carboxylates rearrange to oxazoline-4-imides or 4-carboxylates with high regio and stereo co ntrol. This ring expansion followed by mild hydrolisis allows the synt hesis of enantiomerically pure beta-hydroxy alpha-aminoacid precursors . (C) 1997 Published by Elsevier Science Ltd.