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  Organocatalytic stereoselective cyanosilylation of small ketones

Zhou, H., Zhou, Y., Bae, H. Y., Leutzsch, M., Li, Y., De, C. K., et al. (2022). Organocatalytic stereoselective cyanosilylation of small ketones. Nature, 605, 84-89. doi:10.1038/s41586-022-04531-5.

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 Creators:
Zhou, Hui1, Author              
Zhou, Yu2, Author
Bae, Han Yong1, Author              
Leutzsch, Markus3, Author              
Li, Yihang1, Author              
De, Chandra Kanta1, Author              
Cheng, Gui-Juan2, Author
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Warshel Institute for Computational Biology, School of Life and Health Sciences, The Chinese University of Hong Kong, Shenzhen, Shenzhen, China, ou_persistent22              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 Abstract: Enzymatic stereoselectivity has typically been unrivalled by most chemical catalysts, especially in the conversion of small substrates. According to the ‘lock-and-key theory’1,2, enzymes have confned active sites to accommodate their specifc reacting substrates, a feature that is typically absent from chemical catalysts. An interesting case in this context is the formation of cyanohydrins from ketones and HCN, as this reaction can be catalysed by various classes of catalysts, including biological, inorganic and organic ones3–7. We now report the development of broadly applicable confned organocatalysts for the highly enantioselective cyanosilylation of aromatic and aliphatic ketones, including the challenging 2-butanone. The selectivity (98:2 enantiomeric ratio (e.r.)) obtained towards its pharmaceutically relevant product is unmatched by any other catalyst class, including engineered biocatalysts. Our results indicate that confned chemical catalysts can be designed that are as selective as enzymes in converting small, unbiased substrates, while still providing a broad scope.

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Language(s): eng - English
 Dates: 2021-09-172022-02-082022-05-042022-05-05
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41586-022-04531-5
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Title: Nature
  Abbreviation : Nature
Source Genre: Journal
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Publ. Info: New York : Nature Publishing Group
Pages: - Volume / Issue: 605 Sequence Number: - Start / End Page: 84 - 89 Identifier: ISSN: 25201158
CoNE: https://pure.mpg.de/cone/journals/resource/25201158