Detail View
Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
WEB OF SCIENCE
SCOPUS
- Title
- Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
- Issued Date
- 2022-02
- Citation
- Grossmann, Oleg. (2022-02). Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions. Angewandte Chemie - International Edition, 61(9). doi: 10.1002/anie.202115036
- Type
- Article
- Author Keywords
- Lewis acids ; N-acyliminium ions ; Mukaiyama-Mannich reaction ; imidodiphosphorimidates ; organocatalysis
- Keywords
- REISSERT-TYPE REACTION ; INTERMOLECULAR ADDITION ; GAS-PHASE ; CYCLIZATIONS ; ORGANOCATALYSIS ; HYDROXYLACTAMS ; ALDOLIZATIONS ; NUCLEOPHILES ; DIVERSITY ; CHEMISTRY
- ISSN
- 1433-7851
- 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. © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
더보기
- Publisher
- John Wiley & Sons Ltd.
File Downloads
- There are no files associated with this item.
공유
Total Views & Downloads
???jsp.display-item.statistics.view???: , ???jsp.display-item.statistics.download???: