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Direct enantioselective reduction of C=C bond of β-polyfluoro-alkylated enones via asymmetric photoredox catalysis

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Abstract

Direct enantioselective reduction of the C=C bond of β-polyfluoro-alkylated enones is an important but long-pending subject in asymmetric catalysis. Here, we report on the viability of visible light-driven cooperative photoredox and chiral hydrogen-bonding catalysis to effectively address this challenge, as a variety of products are obtained in high yields (up to 85%) with good to excellent enantioselectivities (up to 98% ee). The formation of thermodynamically favorable enol intermediates after double single-electron reduction represents the center of the success. Additionally, the utility of the current method is validated by the convenient regio-specific and -diverse synthesis of various deuterated derivatives for these products using inexpensive D2O as the deuterium source.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22171072, 21925103, 22301061) and Henan Normal University.

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, 475004, China

    Linghong Zhang, Xiaowei Zhao & Zhiyong Jiang

  2. School of Chemistry and Chemical Engineering, Henan Normal University, Pingyuan Laboratory, Xinxiang, 453007, China

    Jin Ma, Xu Ban, Yanli Yin & Zhiyong Jiang

  3. College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou, 450001, China

    Yanli Yin

Authors
  1. Linghong Zhang
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  2. Jin Ma
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  3. Xu Ban
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  4. Xiaowei Zhao
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  5. Yanli Yin
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  6. Zhiyong Jiang
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Correspondence to Zhiyong Jiang.

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Conflict of interest The authors declare no conflict of interest.

Additional information

Published in virtual special issue “Chiral Photochemistry”

Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2023_1896_MOESM1_ESM.pdf

Supporting Information: Direct Enantioselective Reduction of C=C Bond of β-Polyfluoro-alkylated Enones via Asymmetric Photoredox Catalysis

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Zhang, L., Ma, J., Ban, X. et al. Direct enantioselective reduction of C=C bond of β-polyfluoro-alkylated enones via asymmetric photoredox catalysis. Sci. China Chem. (2024). https://doi.org/10.1007/s11426-023-1896-5

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  • DOI: https://doi.org/10.1007/s11426-023-1896-5

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