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Macroporous Helical Silica Immobilizing Cobalt-Salen Complex Catalyzed Asymmetric Hydrolytic Kinetic Resolution of Epoxides

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Abstract

Based on an entropy-driven principle, new macroporous helical silica rods were synthesized by using mild templates in sol–gel, then functionalized for immobilizing Co-salen complexes to catalyze enantioselective hydrolytic kinetic resolution of epoxides. Characterization revealed both silica supports and heterogeneous Co-salen complexes were macroporous helical materials with affirmative chirality. Catalysis revealed enantioselective adsorption of substrate on silica supports dominated major configuration of resolution products rather than configuration of Co-salen. The (S)-amino alcohol-doped silica and Co-(R,R)salen comprised the most enantioselective combination, which proved chiral synergy between support and Co-salen did exist. This work would contribute to the design of new support materials for asymmetric catalysis.

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Acknowledgments

This work was supported by Fundamental Research Funds for the Central Universities (No. xjj2014005, Application of Mesoporous Helical Support in Catalytic Asymmetric Reactions).

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Authors and Affiliations

  1. Department of Applied Chemistry, School of Science, Xi’an Jiaotong University, No. 28, Xianning West Road, Xi’an, 710049, People’s Republic of China

    Le Li, Benhua Huang, Yu Li, Zulpiya Imam, Aqun Zheng & Yang Sun

  2. School of Pharmacy, Health Science Center, Xi’an Jiaotong University, No. 76, Yanta West Road, Xi’an, 710061, People’s Republic of China

    Guangbin Zhang

Authors
  1. Le Li
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  2. Benhua Huang
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  3. Yu Li
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  4. Guangbin Zhang
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  5. Zulpiya Imam
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  6. Aqun Zheng
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  7. Yang Sun
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Correspondence to Yang Sun.

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Li, L., Huang, B., Li, Y. et al. Macroporous Helical Silica Immobilizing Cobalt-Salen Complex Catalyzed Asymmetric Hydrolytic Kinetic Resolution of Epoxides. Catal Surv Asia 19, 236–248 (2015). https://doi.org/10.1007/s10563-015-9198-y

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