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Enhancing the potential of enantioselective organocatalysis with light

Author

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  • Mattia Silvi

    (School of Chemistry, University of Bristol, Cantock’s Close)

  • Paolo Melchiorre

    (ICIQ, Institute of Chemical Research of Catalonia—the Barcelona Institute of Science and Technology
    ICREA, Catalan Institution for Research and Advanced Studies)

Abstract

Organocatalysis—catalysis mediated by small chiral organic molecules—is a powerful technology for enantioselective synthesis, and has extensive applications in traditional ionic, two-electron-pair reactivity domains. Recently, organocatalysis has been successfully combined with photochemical reactivity to unlock previously inaccessible reaction pathways, thereby creating new synthetic opportunities. Here we describe the historical context, scientific reasoning and landmark discoveries that were essential in expanding the functions of organocatalysis to include one-electron-mediated chemistry and excited-state reactivity.

Suggested Citation

  • Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    • Handle: RePEc:nat:nature:v:554:y:2018:i:7690:d:10.1038_nature25175
    DOI: 10.1038/nature25175
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    Cited by:

    1. Le Zeng & Ling Huang & Wenhai Lin & Lin-Han Jiang & Gang Han, 2023. "Red light-driven electron sacrificial agents-free photoreduction of inert aryl halides via triplet-triplet annihilation," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    2. Guodong Fan & Qingyun Wang & Jun Xu & Pengcheng Zheng & Yonggui Robin Chi, 2023. "Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    3. Le Zeng & Tiexin Zhang & Renhai Liu & Wenming Tian & Kaifeng Wu & Jingyi Zhu & Zhonghe Wang & Cheng He & Jing Feng & Xiangyang Guo & Abdoulkader Ibro Douka & Chunying Duan, 2023. "Chalcogen-bridged coordination polymer for the photocatalytic activation of aryl halides," Nature Communications, Nature, vol. 14(1), pages 1-13, December.
    4. Jing Zhang & Zhao-Xiang Luo & Xia Wu & Chen-Fei Gao & Peng-Yu Wang & Jin-Ze Chai & Miao Liu & Xin-Shan Ye & De-Cai Xiong, 2023. "Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    5. Xiaosheng Yan & Jinlian Cao & Huan Luo & Zhao Li & Zexing Cao & Yirong Mo & Yun-Bao Jiang, 2024. "Heterochiral coupling to bilateral β-turn structured azapeptides bearing two remote chiral centers," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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