ASYMMETRIC-SYNTHESIS OF MESO-2,4-DIAMINOGLUTARIC AND (2R,4R)-2,4-DIAMINOGLUTARIC ACIDS

Authors
AVENOZA A CATIVIELA C PEREGRINA JM ZURBANO MM
Citation
A. Avenoza et al., ASYMMETRIC-SYNTHESIS OF MESO-2,4-DIAMINOGLUTARIC AND (2R,4R)-2,4-DIAMINOGLUTARIC ACIDS, Tetrahedron : asymmetry, 8(6), 1997, pp. 863-871
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
6
Year of publication
1997
Pages
863 - 871
Database
ISI
SICI code
0957-4166(1997)8:6<863:AOMA(>2.0.ZU;2-#
Abstract
In order to synthesize meso- and (2R,4R)-2,4-diaminoglutaric acids, a synthetic route has been developed starting from Garner's aldehyde and where the key steps are the asymmetric hydrogenations of (E)- and ido )-2'-(methoxycarbonyl)ethenyl]-1,3-oxazolidine, under heterogeneous co nditions, followed by oxidation and further hydrolysis. A model is pro posed to explain the stereochemical outcome of the asymmetric hydrogen ation. (C) 1997 Elsevier Science Ltd.