AN EFFICIENT AND STEREOSPECIFIC SYNTHESIS OF (2S,4S)-2,4-DIAMINOGLUTARIC ACID

Authors
TANAKA K SAWANISHI H
Citation
K. Tanaka et H. Sawanishi, AN EFFICIENT AND STEREOSPECIFIC SYNTHESIS OF (2S,4S)-2,4-DIAMINOGLUTARIC ACID, Tetrahedron : asymmetry, 9(1), 1998, pp. 71-77
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
1
Year of publication
1998
Pages
71 - 77
Database
ISI
SICI code
0957-4166(1998)9:1<71:AEASSO>2.0.ZU;2-J
Abstract
An efficient and stereospecific synthesis of (2S,4S)-2,4-diaminoglutar ic acid 1 starting from trans-4-hydroxy-L-proline 2 is presented. The key step involves the combined application of ruthenium tetroxide (RuO 4) oxidation of 4-(tert-butoxycarbonylamino)proline derivatives 7 and 8 followed by regioselective ring opening of the resulting lactams 9 a nd 10 with 1 M LiOH. (C) 1998 Elsevier Science Ltd. All rights reserve d.