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Regio- and Enantioselective Epoxy Ring Opening of 2,3-Epoxy-3-phenyl Alcohols/Carboxylic Acids and Their Derivatives

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Abstract

The review highlights the progress of ring opening of 2,3-epoxy-3-phenyl alcohols/carboxylic acids and their derivatives over the past few decades. The presence of a phenyl group in epoxy alcohols/carboxylic acids make ring opening more complicated due to increase of steric hindrance and polarity. The varieties of methods for catalysis, organic solvent/water solvent and Lewis acid/base incorporation of epoxy groups into the target moiety attract more attention. In the ring-opening reaction of epoxides with water, alcohols, amines, ammonia, phenols, hydrogen halides, acids and thiols, the use of significant catalytic systems and appropriate solvents is often put into consideration firstly. Ring-opening reactions of epoxides in the presence of catalysts need to be explored, including 2,3-epoxy phenyl alcohols, phenylglycidyl ethers, and other conversions. The review will throw light on these reactions and inspire more efforts into the development of new ring opening reactions of epoxides.

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Funding

This work was supported by the Luzhou Southwest Medical University Joint Project (2018 LZXNYD-ZK04), by the Luzhou Science and Technology Plan Project [2017-S-39(5/5)], and by the Collaborative Fund of Luzhou Municipal Government and Sichuan University (2018CDLZ-13).

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  1. Department of Pharmacy, School of Pharmaceutical Science, Southwest Medical University, 646000, Luzhou, China

    Xiaoyan Zhan

  2. Department of Chemistry, School of Basic Medical Science, Southwest Medical University, 646000, Luzhou, China

    Xi Du

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Zhan, X., Du, X. Regio- and Enantioselective Epoxy Ring Opening of 2,3-Epoxy-3-phenyl Alcohols/Carboxylic Acids and Their Derivatives. Russ J Org Chem 56, 679–692 (2020). https://doi.org/10.1134/S107042802004017X

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