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Oxazolidinone Synthesis through Halohydrin Dehalogenase‐ Catalyzed Dynamic Kinetic Resolution
Author(s) -
Mikleušević Ana,
Hameršak Zdenko,
SalopekSondi Branka,
Tang Lixia,
Janssen Dick B.,
Majerić Elenkov Maja
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500111
Subject(s) - chemistry , kinetic resolution , cyanate , racemization , catalysis , dehalogenase , substrate (aquarium) , bromide , reagent , combinatorial chemistry , enzyme , stereochemistry , organic chemistry , enantioselective synthesis , oceanography , geology
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.