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  Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions

Grossmann, O., Maji, R., Aukland, M. H., Lee, S., & List, B. (2022). Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions. Angewandte Chemie International Edition, 61(9): e202115036. doi:10.1002/anie.202115036.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0009-B5EB-2 Version Permalink: https://hdl.handle.net/21.11116/0000-000A-2807-2
Genre: Journal Article

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Grossmann-Maji-Aukland-Lee-List.pdf (Publisher version), 7MB
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 Creators:
Grossmann, Oleg1, Author           
Maji, Rajat1, Author           
Aukland, Miles H.1, Author           
Lee, Sunggi2, Author
List, Benjamin1, 3, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Department of Emerging Materials Science, Daegu Gyeongbuk Institute of Science and Technology (DGIST), 333, Techno Jungang-daero, Hyeonpung-myeon, Dalseong-gun, Daegu (Republik of Korea), ou_persistent22              
3Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, 001-0021 Japan, ou_persistent22              

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Free keywords: Lewis acids; N-acyliminium ions; Mukaiyama-Mannich reaction; imidodiphosphorimidates; organocatalysis
 Abstract: Strong and confined imidodiphosphorimidate (IDPi) catalysts enable highly enantioselective substitutions of cyclic, aliphatic hemiaminal ethers with enol silanes. 2-Substituted pyrrolidines, piperidines, and azepanes are obtained with high enantioselectivities, and the method displays a broad tolerance of various enol silane nucleophiles. Several natural products can be accessed using this methodology. Mechanistic studies support the intermediacy of non-stabilized, cyclic N- ( exo -acyl)iminium ions, paired with the confined chiral counteranion. Computational studies suggest transition states that explain the observed enantioselectivity.

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Language(s): eng - English
 Dates: 2021-11-052021-12-032021-12-122022-02-21
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202115036
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (9) Sequence Number: e202115036 Start / End Page: - Identifier: CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851