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One-pot remote desymmetrization/peterson-olefination for the construction of silicon-stereogenic silyl ethers

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Abstract

Chiral silyl ethers and silanols are important synthetic intermediates and bioactive compounds. In this work, we developed a one-pot remote desymmetrization/Peterson-olefination of silacyclopentene oxides with benzoic acids in the presence of Martin’s sulfurane. This new methodology not only realizes the atom-economy of Peterson olefination, but also represents a catalytic method for synthesis of silicon-stereogenic silyl ethers. Using a bulky chiral phosphoric acid 4i as organocatalyst, the reactions proceeded efficiently to afford various olefin-functionalized organosilyl ethers in excellent diastereoelectivities (up to 25/1 d.r.) and high enantioselectivities (up to 94% ee).

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22271276, 21871254, 21702203) and the National Key Research and Development Program of China (2022YFC2105900).

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Authors and Affiliations

  1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    Wengang Guo, Qian Li, Yan Liu & Can Li

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  1. Wengang Guo
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  2. Qian Li
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  3. Yan Liu
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  4. Can Li
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Correspondence to Yan Liu or Can Li.

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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 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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Guo, W., Li, Q., Liu, Y. et al. One-pot remote desymmetrization/peterson-olefination for the construction of silicon-stereogenic silyl ethers. Sci. China Chem. 66, 2797–2802 (2023). https://doi.org/10.1007/s11426-023-1643-7

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  • DOI: https://doi.org/10.1007/s11426-023-1643-7

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