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Synthesis of chiral allylic phosphonates via asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides

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Abstract

Chiral phosphine-containing skeletons play a pivotal role in bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. Despite considerable progress has been made in the synthesis of chiral phosphorus compounds, the development of facile and modular methods to access chiral allylic phosphorus compounds remains challenging due to the simultaneous control required for reactivity, enantioselectivity, and stereoselectivity. Herein, we present a general and modular platform to achieve the asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides, enabling the synthesis of highly valuable chiral allylic phosphonate products with remarkable yields, enantioselectivities, and stereoselectivities.

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Change history

  • 19 October 2023

    The corresponding author Tao Xu to Tao XU has been updated.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22071183) and the Science and Technology Commission of Shanghai Municipality (19DZ2271500).

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Authors and Affiliations

  1. Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai, 200092, China

    Hepan Wang, Xinxuan Li & Tao XU

Authors
  1. Hepan Wang
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  2. Xinxuan Li
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  3. Tao XU
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Corresponding author

Correspondence to Tao XU.

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Conflict of interest The authors declare no conflict of interest.

Additional information

Supporting information The supporting information is available online at https://chem.scichina.com and https://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_1726_MOESM1_ESM.pdf

Synthesis of Chiral Allylic Phosphonates via Asymmetric Reductive Cross-Coupling of α-Bromophosphonates and Vinyl Bromides

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Wang, H., Li, X. & XU, T. Synthesis of chiral allylic phosphonates via asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides. Sci. China Chem. 66, 2621–2625 (2023). https://doi.org/10.1007/s11426-023-1726-1

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  • DOI: https://doi.org/10.1007/s11426-023-1726-1

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