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Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

MPS-Authors
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Zhou,  Hui
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Han,  Jung Tae
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Nöthling,  Nils
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lindner,  Monika M.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Tsuji,  Nobuya
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zhang,  Li
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Zhou, H., Han, J. T., Nöthling, N., Lindner, M. M., Jenniches, J., Kühn, C., et al. (2022). Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers. Journal of the American Chemical Society. doi:10.1021/jacs.2c04261.


Cite as: https://hdl.handle.net/21.11116/0000-000A-9583-9
Abstract
Functionalized enantiopure organosilanes are important building blocks with applications in various fields of chemistry; nevertheless, asymmetric synthetic methods for their preparation are rare. Here we report the first organocatalytic enantioselective synthesis of tertiary silyl ethers possessing “central chirality” on silicon. The reaction proceeds via a desymmetrizing carbon–carbon bond forming silicon–hydrogen exchange reaction of symmetrical bis(methallyl)silanes with phenols using newly developed imidodiphosphorimidate (IDPi) catalysts. A variety of enantiopure silyl ethers was obtained in high yields with good chemo- and enantioselectivities and could be readily derivatized to several useful chiral silicon compounds, leveraging the olefin functionality and the leaving group nature of the phenoxy substituent.