Synthesis of both enantiomers of 4-vinyl oxazolidin-2-one from a single precursor: D-isoascorbic acid

Authors
Delle Monache, G Misiti, D Salvatore, P Zappia, G
Citation
G. Delle Monache et al., Synthesis of both enantiomers of 4-vinyl oxazolidin-2-one from a single precursor: D-isoascorbic acid, CHIRALITY, 12(3), 2000, pp. 143-148
Citations number
24
Categorie Soggetti
Chemistry & Analysis
Journal title
CHIRALITY
ISSN journal
08990042 → ACNP
Volume
12
Issue
3
Year of publication
2000
Pages
143 - 148
Database
ISI
SICI code
0899-0042(2000)12:3<143:SOBEO4>2.0.ZU;2-Z
Abstract
A convenient synthesis of (S)- and (R)-4-vinyl oxazolidin-2-one 1 and 2 fro m the same inexpensive starting material, D-isoascorbic acid, is described. The title compounds were obtained in 44% and 38% yield, respectively, by o perationally simple steps. This approach is a suitable alternative to the l iterature methods and enhances the synthetic utility of these intermediates . Chirality 12:143-148, 2000. (C) 2000 Wiley-Liss, Inc.