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  Organocatalytic DYKAT of Si-Stereogenic Silanes

Zhou, H., Properzi, R., Leutzsch, M., Belanzoni, P., Bistoni, G., Tsuji, N., et al. (2023). Organocatalytic DYKAT of Si-Stereogenic Silanes. Journal of the American Chemical Society, 145(9), 4994-5000. doi:10.1021/jacs.3c00858.

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 Creators:
Zhou, Hui1, Author           
Properzi, Roberta1, Author           
Leutzsch, Markus2, Author           
Belanzoni, Paola3, Author
Bistoni, Giovanni3, Author           
Tsuji, Nobuya4, Author           
Han, Jung Tae1, Author           
Zhu, Chendan1, Author           
List, Benjamin1, 4, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              
3University of Perugia, Department of Chemistry, Biology and Biotechnology, 06122 Perugia, Italy, ou_persistent22              
4Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo 001-0021, Japan, ou_persistent22              

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 Abstract: Chiral organosilanes do not exist in nature and are therefore absent from the “chiral pool”. As a consequence, synthetic approaches toward enantiopure silanes, stereogenic at silicon, are rather limited. While catalytic asymmetric desymmetrization reactions of symmetric organosilicon compounds have been developed, the utilization of racemic silanes in a dynamic kinetic asymmetric transformation (DYKAT) or dynamic kinetic resolution (DKR) would significantly expand the breadth of accessible Si-stereogenic compounds. We now report a DYKAT of racemic allyl silanes enabled by strong and confined imidodiphosphorimidate (IDPi) catalysts, providing access to Si-stereogenic silyl ethers. The products of this reaction are easily converted into useful enantiopure monohydrosilanes. We propose a spectroscopically and experimentally supported mechanism involving the epimerization of a catalyst-bound intermediate.

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Language(s): eng - English
 Dates: 2023-01-222023-02-242023-03-08
 Publication Status: Issued
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.3c00858
 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: 145 (9) Sequence Number: - Start / End Page: 4994 - 5000 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870