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  Harnessing the ambiphilicity of silyl nitronates in a catalytic asymmetric approach to aliphatic β3-amino acids

Das, S., Mitschke, B., De, C. K., Harden, I., Bistoni, G., & List, B. (2021). Harnessing the ambiphilicity of silyl nitronates in a catalytic asymmetric approach to aliphatic β3-amino acids. Nature Catalysis, 4(12), 1043-1049. doi:10.1038/s41929-021-00714-x.

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Das, Mitschke, De, Harden, Bistoni, List 2021.pdf (Postprint), 2MB
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Das, Mitschke, De, Harden, Bistoni, List 2021.pdf
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 Creators:
Das, Sayantani1, Author              
Mitschke, Benjamin1, Author              
De, Chandra Kanta1, Author              
Harden, Ingolf2, Author              
Bistoni, Giovanni2, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541703              

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Free keywords: Asymmetric catalysis; Synthetic chemistry methodology; Organocatalysis
 Abstract: Nitronate anions, formally generated by α-deprotonating the corresponding nitroalkanes, are highly nucleophilic and versatile intermediates in many carbon–carbon bond-forming reactions. In contrast, the corresponding silyl nitronates are ambiphilic and react, at the same carbon atom, with both electrophiles and nucleophiles. However, while their nucleophilicity has been well exploited in catalytic enantioselective reactions with imines and aldehydes, utilizing the electrophilicity of silyl nitronates in asymmetric synthesis has remained elusive. Here we report the facile, efficient and general reactivity of readily available silyl nitronates with silyl ketene acetals, catalysed by highly Lewis-acidic and confined silylium imidodiphosphorimidate catalysts. The products of this reaction, so-called nitroso acetals, are obtained in excellent enantioselectivity and can be easily converted into N-Boc-β3-amino acid esters in a single step.

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Language(s): eng - English
 Dates: 2020-07-172021-10-252021-12-02
 Publication Status: Published online
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41929-021-00714-x
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Title: Nature Catalysis
  Abbreviation : Nat. Catal.
Source Genre: Journal
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Publ. Info: New York : Nature Publishing Group
Pages: - Volume / Issue: 4 (12) Sequence Number: - Start / End Page: 1043 - 1049 Identifier: ISSN: 25201158
CoNE: https://pure.mpg.de/cone/journals/resource/25201158