ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION - SYNTHESIS OF N-PROTECTED (4S)-4-HYDROXY L-GLUTAMIC ACID DIESTER

Authors
GEFFLAUT T BAUER U AIROLA K KOSKINEN AMP
Citation
T. Gefflaut et al., ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION - SYNTHESIS OF N-PROTECTED (4S)-4-HYDROXY L-GLUTAMIC ACID DIESTER, Tetrahedron : asymmetry, 7(11), 1996, pp. 3099-3102
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
11
Year of publication
1996
Pages
3099 - 3102
Database
ISI
SICI code
0957-4166(1996)7:11<3099:A1C-SO>2.0.ZU;2-2
Abstract
An asymmetric synthesis of N-protected (4S)-4-hydroxy L-glutamic acid diester is described. The key feature of the synthesis is the asymmetr ic 1,3-dipolar cycloaddition of nitrone 4 with 5, which provides stere oselectively the isoxazolidine with the correct stereochemistry suitab le for the synthesis of N-protected (4S)-4-hydroxy L-glutamic acid die ster 1. Copyright (C) 1996 Elsevier Science Ltd