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Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of α-dehydro amino ketones

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Abstract

A series of novel atropisomeric diphosphine ligands termed TanPhos were designed and synthesized, which has a smaller bite angle compared with that of other ligands such as BINAP. TanPhos showed high reactivity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of a-dehydro amino ketones, and up 99% yield and 99% ee were obtained for a wide range of chiral α-amino ketones.

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Acknowledgements

X. Zhang acknowledges the National Key R&D Program of China (2021YFA1500201), the Stable Support Plan Program of Shenzhen Natural Science Fund (20200925161222002), the Key-Area Research and Development Program of Guangdong Province (2020B010188001), the Innovative Team of Universities in Guangdong Province (2020KCXTD016), and the National Natural Science Foundation of China (21991113). G.-Q. Chen gratefully acknowledges the Guangdong Basic and Applied Basic Research Foundation (2022B1515020055), the National Natural Science Foundation of China (22171129) and Shenzhen Science and Technology Innovation Committee (JCYJ20210324104202007) for financial support.

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China

    Xuefeng Tan, Shuang Gao, Chunyan Yang, Qiwei Lang, Xiaobing Ding & Xumu Zhang

  2. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, 518000, China

    Gen-Qiang Chen

  3. Department of Chemistry, City University of Hong Kong, Hong Kong, 999077, China

    Xuefeng Tan

Authors
  1. Xuefeng Tan
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  2. Shuang Gao
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  3. Chunyan Yang
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  4. Qiwei Lang
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  5. Xiaobing Ding
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  6. Gen-Qiang Chen
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  7. Xumu Zhang
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Corresponding authors

Correspondence to Xuefeng Tan, Xiaobing Ding, Gen-Qiang Chen or Xumu Zhang.

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Conflict of interest The authors declare no conflict of interest.

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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_1798_MOESM1_ESM.pdf

Design and Synthesis of Novel 1,3-Diene Bridged Chiral Atropoisomeric Diphosphine Ligands for Asymmetric Hydrogenation of α-Dehydro Amino Ketones

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Tan, X., Gao, S., Yang, C. et al. Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of α-dehydro amino ketones. Sci. China Chem. 66, 2847–2851 (2023). https://doi.org/10.1007/s11426-023-1798-1

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  • DOI: https://doi.org/10.1007/s11426-023-1798-1

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