Epoxide Hydrolase-Catalyzed Enantioselective Synthesis of Chiral 1,2-Diols via Desymmetrization of meso-Epoxides

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• 作者：Lishan Zhao ; Bin Han ; Zilin Huang ; Mark Miller ; Hongjun Huang ; Dan S. Malashock ; Zuolin Zhu ; Aileen Milan ; Dan E. Robertson ; David P. Weiner ; and Mark J. Burk
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：September 15, 2004
• 年：2004
• 卷：126
• 期：36
• 页码：11156 - 11157
• 全文大小：56K
• 年卷期：v.126,no.36(September 15, 2004)
• ISSN：1520-5126

文摘

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.