Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides

Authors
Spelberg, JHL Vlieg, JETV Tang, LX Janssen, DB Kellogg, RM
Citation
Jhl. Spelberg et al., Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides, ORG LETT, 3(1), 2001, pp. 41-43
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
1
Year of publication
2001
Pages
41 - 43
Database
ISI
SICI code
1523-7060(20010111)3:1<41:HEARBA>2.0.ZU;2-Q
Abstract
[GRAPHICS] The halohydrin dehalogenase from Agrobacterium radiobacter AD1 catalyzed th e highly enantioselective and beta -regioselective azidolysis of (substitut ed) styrene oxides. By means of kinetic resolutions the remaining epoxide a nd the formed azido alcohol could be obtained in very high ee. In a large s cale conversion, the decrease in yield and selectivity due to the uncatalyz ed chemical side reaction could be overcome by slow addition of azide.