Organocatalytic stereoselective cyanosilylation of small ketones

Hui Zhou, Yu Zhou, Han Yong Bae, Markus Leutzsch, Yihang Li, Chandra Kanta De, Gui-Juan Cheng () and Benjamin List ()
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Hui Zhou: Max-Planck-Institut für Kohlenforschung
Yu Zhou: The Chinese University of Hong Kong, Shenzhen
Han Yong Bae: Max-Planck-Institut für Kohlenforschung
Markus Leutzsch: Max-Planck-Institut für Kohlenforschung
Yihang Li: Max-Planck-Institut für Kohlenforschung
Chandra Kanta De: Max-Planck-Institut für Kohlenforschung
Gui-Juan Cheng: The Chinese University of Hong Kong, Shenzhen
Benjamin List: Max-Planck-Institut für Kohlenforschung

Nature, 2022, vol. 605, issue 7908, 84-89

Abstract: 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 confined active sites to accommodate their specific 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 confined 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 confined chemical catalysts can be designed that are as selective as enzymes in converting small, unbiased substrates, while still providing a broad scope.

Date: 2022
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DOI: 10.1038/s41586-022-04531-5

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