ArticleAngewandte Chemie (International ed. in English)2022
Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- Integrated Life Cycle Assessment Guides Sustainability in Synthesis: Antiviral Letermovir as a Case Study.Journal of the American Chemical Society · 2025Article
- Regioselective Substitution of BINOL.Chemical reviews · 2024Review
- Interrogating the Crucial Interactions at Play in the Chiral Cation-Directed Enantioselective Borylation of Arenes.ACS catalysis · 2023Article
- Asymmetric Catalytic Friedel-Crafts Reactions of Unactivated Arenes.Journal of the American Chemical Society · 2023Article
- A Catalytic Asymmetric Hydrolactonization.Journal of the American Chemical Society · 2023Article
- Organocatalytic DYKAT ofJournal of the American Chemical Society · 2023Article
- Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions.Angewandte Chemie (International ed. in English) · 2022Article
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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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