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Asymmetric radical carboesterification of dienes

Author

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  • Xiaotao Zhu

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Wujun Jian

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Meirong Huang

    (Peking University Shenzhen Graduate School)

  • Daliang Li

    (College of Life Sciences, Fujian Normal University)

  • Yajun Li

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Xinhao Zhang

    (Peking University Shenzhen Graduate School)

  • Hongli Bao

    (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

The straightforward strategy of building a chiral C-O bond directly on a general carbon radical center is challenging and stereocontrol of the reactions of open-chain hydrocarbon radicals remains a largely unsolved problem. Advance in this elementary step will spur the development of asymmetric radical C-O bond construction. Herein, we report a copper-catalyzed regioselective and enantioselective carboesterification of substituted dienes using alkyl diacyl peroxides as the source of both the carbon and oxygen substituents. The participation of external acids in this reaction substantially extends its applicability and leads to structurally diverse allylic ester products. This work represents the advance in the key elementary reaction of intermolecular enantioselective construction of C-O bond on open-chain hydrocarbon radicals and may lead to the discovery of other asymmetric radical reactions.

Suggested Citation

  • Xiaotao Zhu & Wujun Jian & Meirong Huang & Daliang Li & Yajun Li & Xinhao Zhang & Hongli Bao, 2021. "Asymmetric radical carboesterification of dienes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26843-2
    DOI: 10.1038/s41467-021-26843-2
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    References listed on IDEAS

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    1. Zhaobin Wang & Haolin Yin & Gregory C. Fu, 2018. "Catalytic enantioconvergent coupling of secondary and tertiary electrophiles with olefins," Nature, Nature, vol. 563(7731), pages 379-383, November.
    2. Caiyou Chen & Jonas C. Peters & Gregory C. Fu, 2021. "Photoinduced copper-catalysed asymmetric amidation via ligand cooperativity," Nature, Nature, vol. 596(7871), pages 250-256, August.
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    Cited by:

    1. Ting Wan & Luca Capaldo & Jonas Djossou & Angela Staffa & Felix J. Zwart & Bas Bruin & Timothy Noël, 2024. "Rapid and scalable photocatalytic C(sp2)–C(sp3) Suzuki−Miyaura cross-coupling of aryl bromides with alkyl boranes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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