Enzymatic and chiral HPLC resolution of alpha-azido acids and amides

Citation
Cw. Tornoe et al., Enzymatic and chiral HPLC resolution of alpha-azido acids and amides, TETRAHEDR-A, 11(5), 2000, pp. 1239-1248
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
5
Year of publication
2000
Pages
1239 - 1248
Database
ISI
SICI code
0957-4166(20000324)11:5<1239:EACHRO>2.0.ZU;2-U
Abstract
For the first time, enzymatic resolution of alpha-azido acid amides has bee n successfully demonstrated with high yields and enantiomeric excess. In on e case dynamic kinetic resolution was achieved leading to more than 50% yie ld of the enantiomerically pure azido acid. Chiral HPLC was also used to se parate racemic alpha-azido acids and the separation process was automated. Two routes to enantiopure alpha-azido acid building blocks for solid-phase peptide synthesis have, therefore, been established. (C) 2000 Elsevier Scie nce Ltd. All rights reserved.