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  Catalytic enantiocontrol over a non-classical carbocation

Properzi, R., Kaib, P. S., Leutzsch, M., Pupo, G., Mitra, R., De, C. K., et al. (2020). Catalytic enantiocontrol over a non-classical carbocation. Nature Chemistry. doi:10.1038/s41557-020-00558-1.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0007-3108-9 Version Permalink: http://hdl.handle.net/21.11116/0000-0007-3109-8
Genre: Journal Article

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 Creators:
Properzi, Roberta1, Author              
Kaib, Philip S.J.1, Author              
Leutzsch, Markus2, Author              
Pupo, Gabriele1, Author              
Mitra, Raja1, Author              
De, Chandra Kanta1, Author              
Song, Lijuan3, Author
Schreiner, Peter R.3, Author
List, Benjamin1, 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              
3Institute of Organic Chemistry, Justus Liebig University, Giessen, Germany, ou_persistent22              

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Free keywords: Asymmetric catalysis; Organocatalysis; Stereochemistry
 Abstract: Carbocations can be categorized into classical carbenium ions and non-classical carbonium ions. These intermediates are ubiquitous in reactions of both fundamental and practical relevance, finding application in the petroleum industry as well as the discovery of new drugs and materials. Conveying stereochemical information to carbocations is therefore of interest to a range of chemical fields. While previous studies targeted systems proceeding through classical ions, enantiocontrol over their non-classical counterparts has remained unprecedented. Here we show that strong and confined chiral acids catalyse enantioselective reactions via the non-classical 2-norbornyl cation. This reactive intermediate is generated from structurally different precursors by leveraging the reactivity of various functional groups to ultimately deliver the same enantioenriched product. Our work demonstrates that tailored catalysts can act as suitable hosts for simple, non-functionalized carbocations via a network of non-covalent interactions. We anticipate that the methods described herein will provide catalytic accessibility to valuable carbocation systems.

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Language(s): eng - English
 Dates: 2019-12-272020-08-212020-09-28
 Publication Status: Published online
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41557-020-00558-1
 Degree: -

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Title: Nature Chemistry
  Abbreviation : Nat. Chem.
Source Genre: Journal
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Publ. Info: London, UK : Nature Publishing Group
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 1755-4330
CoNE: https://pure.mpg.de/cone/journals/resource/1755-4330