Oxazoline-N-oxide mediated asymmetric cycloadditions. Recent progress in the stereoselective syntheses of beta-lactones and beta-lactams

Authors
Dirat, O Kouklovsky, C Mauduit, M Langlois, Y
Citation
O. Dirat et al., Oxazoline-N-oxide mediated asymmetric cycloadditions. Recent progress in the stereoselective syntheses of beta-lactones and beta-lactams, PUR A CHEM, 72(9), 2000, pp. 1721-1737
Citations number
23
Categorie Soggetti
Chemistry
Journal title
PURE AND APPLIED CHEMISTRY
ISSN journal
00334545 → ACNP
Volume
72
Issue
9
Year of publication
2000
Pages
1721 - 1737
Database
ISI
SICI code
0033-4545(200009)72:9<1721:OMACRP>2.0.ZU;2-#
Abstract
Camphor-derived oxazoline-N-oxides are versatile dipoles in a new kind of a symmetric [2+3] cycloadditions. Recent applications of this methodology all owed the stereoselective syntheses of several beta -lactones natural produc ts such as 1233A and tetrahydrolipstatine. Two formal syntheses of beta -la ctams antibiotics, beta -methyl thienamycin and carpetimycin A, have also b een achieved using this type of cycloaddition.