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- Title
Oxazolidinone Synthesis through Halohydrin Dehalogenase- Catalyzed Dynamic Kinetic Resolution.
- Authors
Mikleušević, Ana; Hameršak, Zdenko; Salopek ‐ Sondi, Branka; Tang, Lixia; Janssen, Dick B.; Majerić Elenkov, Maja
- Abstract
An efficient dynamic kinetic resolution protocol using a single enzyme is described. Both the kinetic resolution and substrate racemization are catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC). The HheC-catalyzed reaction of epibromohydrin and 2-bromomethyl-2-methyloxirane with sodium cyanate afforded 5-substituted 2-oxazolidinones in high yields (97% and 87%) and high optical purity (89% and >99% ee) in the presence of catalytic amounts of bromide ion. These compounds are valuable building blocks with diverse synthetic applications.
- Subjects
OXAZOLIDINONES synthesis; HALOHYDRINS; DEHALOGENASES; KINETIC resolution; RACEMIZATION
- Publication
Advanced Synthesis & Catalysis, 2015, Vol 357, Issue 8, p1709
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201500111