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  Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

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.

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 Creators:
Zhou, Hui1, Author           
Han, Jung Tae1, Author           
Nöthling, Nils2, Author           
Lindner, Monika M.1, Author           
Jenniches, Judith3, Author
Kühn, Clemens3, Author
Tsuji, Nobuya1, Author           
Zhang, Li4, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
3Innovation Center, Merck KGaA, Frankfurter Straße 250, 64293 Darmstadt, Germany, ou_persistent22              
4Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              

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 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.

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Language(s): eng - English
 Dates: 2022-04-212022-06-01
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.2c04261
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870