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Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation

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Abstract

Chiral homoallylic vicinal diols are found in many bioactive compounds and are among the most versatile functional groups in organic chemistry. Here, we describe an asymmetric carbonyl allylation of aldehydes with allyl ethers proceeding via allylic C-H borylation enabled by palladium and chiral phosphoric acid sequential catalysis, providing facile access to homoallylic vicinal anti-diols in high yields and with excellent stereoselectivity. This protocol enables the total synthesis of aigialomycin D to be finished within 7 steps.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21831007). We sincerely thank the group of SIOC for providing high-resolution MS analysis.

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Authors and Affiliations

  1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

    Tian-Ci Wang, Pu-Sheng Wang, Dian-Feng Chen & Liu-Zhu Gong

  2. Center for Excellence in Molecular Synthesis of CAS, Hefei, 230026, China

    Liu-Zhu Gong

Authors
  1. Tian-Ci Wang
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  2. Pu-Sheng Wang
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  3. Dian-Feng Chen
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  4. Liu-Zhu Gong
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Correspondence to Liu-Zhu Gong.

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The authors declare no conflict of interest.

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The supporting information is available online at http://chem.scichina.com and http://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_2021_1134_MOESM1_ESM.doc

Access to Chiral Homoallylic Vicinal Diols from Carbonyl Allylation of Aldehydes with Allyl ethers via Palladium-catalyzed Allylic C-H Borylation

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Wang, TC., Wang, PS., Chen, DF. et al. Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation. Sci. China Chem. 65, 298–303 (2022). https://doi.org/10.1007/s11426-021-1134-x

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  • DOI: https://doi.org/10.1007/s11426-021-1134-x

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