SYNTHESIS OF ALPHA-HYDROXY-BETA-AMINO ACIDS FROM CHIRAL CYANOHYDRLNS

Authors
WARMERDAM EGJC VANRIJN RD BRUSSEE J KRUSE CG VANDERGEN A
Citation
Egjc. Warmerdam et al., SYNTHESIS OF ALPHA-HYDROXY-BETA-AMINO ACIDS FROM CHIRAL CYANOHYDRLNS, Tetrahedron : asymmetry, 7(6), 1996, pp. 1723-1732
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
6
Year of publication
1996
Pages
1723 - 1732
Database
ISI
SICI code
0957-4166(1996)7:6<1723:SOAAFC>2.0.ZU;2-0
Abstract
(-)-(R,E)-2-hydroxy-3-pentenenitrile 1, obtained by R-oxynitrilase cat alyzed addition of HCN to 2-butenal, was shown to be an excellent chir al starting material for the synthesis of alpha-hydroxy-beta-amino aci ds of high enantiomeric and diastereomeric purity. The synthesis of N- benzyl (S)-isoserine 7a and (2S,3S)-isoallothreonine 7b, as well as N- benzoyl (2S,3S)-3-phenylisoserine 14 is reported. Copyright (C) 1996 E lsevier Science Ltd