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Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes

Author

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  • Tianbao Hu

    (Sichuan University)

  • Chen Zhao

    (Sichuan University)

  • Yan Zhang

    (Sichuan University)

  • Yuzhong Kuang

    (China Pharmaceutical University)

  • Lu Gao

    (Sichuan University)

  • Wanshu Wang

    (Sichuan University)

  • Zhishan Su

    (Sichuan University)

  • Zhenlei Song

    (Sichuan University)

Abstract

Organosilanes possessing an enantioenriched stereogenic silicon center are important in many branches of chemistry, yet they remain challenging to synthesize in a practical and scalable way. Here we report a dynamic kinetic silyletherification process of racemic chlorosilanes with (S)-lactates using 4-aminopyridine as a Lewis base catalyst. This enantioconvergent approach asymmetrically constructs the stereogenic silicon center in a different manner from traditional resolution or desymmetrization. A range of silylethers have been prepared with high diastereoselectivity on up to 10 g-scale, allowing the practical synthesis of diverse enantioenriched organosilane analogs.

Suggested Citation

  • Tianbao Hu & Chen Zhao & Yan Zhang & Yuzhong Kuang & Lu Gao & Wanshu Wang & Zhishan Su & Zhenlei Song, 2023. "Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40558-6
    DOI: 10.1038/s41467-023-40558-6
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    References listed on IDEAS

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    1. Kun An & Wenpeng Ma & Li-Chuan Liu & Tao He & Guiyu Guan & Qing-Wei Zhang & Wei He, 2022. "Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
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    Cited by:

    1. Yu Yan & Qi Wei & Zhishan Su & Nan-Nan Hang & Tamio Hayashi & Jialin Ming, 2024. "Carbon-silicon-switch effect in enantioselective construction of silicon-stereogenic center from silacyclohexadienones," Nature Communications, Nature, vol. 15(1), pages 1-13, December.

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