Epoxide Hydrolase-Catalyzed Enantioselective Synthesis of Chiral 1,2-Diols via Desymmetrization of m eso -Epoxides
Journal of the American Chemical Society2004Vol. 126(36), pp. 11156–11157
Citations Over TimeTop 14% of 2004 papers
Lishan Zhao, Bin Han, Zilin Huang, Mark A. Miller, Hongjun Huang, Dan S. Malashock, Zuolin Zhu, Aileen Milan, Dan E. Robertson, David P. Weiner, Mark J. Burk
Abstract
The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as acyclic alkyl- and aryl-substituted substrates, is demonstrated. The chiral (R,R)-diols were furnished with high ee's and yields. The discovery of the first microbial epoxide hydrolases providing access to complementary (S,S)-diols is also described.
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