STEREOSELECTIVE SYNTHESIS OF RACEMIC ALPHA-AMINO-ACID DERIVATIVES WITH A BETA-LACTAM SKELETON - APPLICATION OF THE STAUDINGER REACTION TO CHIRAL IMINES OF METHYL GLYOXYLATE

Authors
BARREAU M COMMERCON A MIGNANI S MOUYSSET D PERFETTI P STELLA L
Citation
M. Barreau et al., STEREOSELECTIVE SYNTHESIS OF RACEMIC ALPHA-AMINO-ACID DERIVATIVES WITH A BETA-LACTAM SKELETON - APPLICATION OF THE STAUDINGER REACTION TO CHIRAL IMINES OF METHYL GLYOXYLATE, Tetrahedron, 54(38), 1998, pp. 11501-11516
Citations number
62
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
38
Year of publication
1998
Pages
11501 - 11516
Database
ISI
SICI code
0040-4020(1998)54:38<11501:SSORAD>2.0.ZU;2-N
Abstract
Selected imines of methyl glyoxylate act as good partners in the Staud inger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substitu ted ketenes, but the asymmetric induction is low when imines derived F rom chiral 1-aryl-ethylamines are used. (C) 1998 Elsevier Science Ltd. All rights reserved.