ArticleAngewandte Chemie (International ed. in English)2017
Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Stereoselective Synthesis of Aminals Through Enzyme-Catalyzed Intermolecular C(spAngewandte Chemie (International ed. in English) · 2026Article
- Deconstructing α-Amidoalkyl Sulfones as DualThe Journal of organic chemistry · 2025Article
- Dinuclear Zn-Catalytic System as Brønsted Base and Lewis Acid for Enantioselectivity in Same Chiral Environment.ACS omega · 2024Review
- Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-Organic letters · 2020Article
- Catalytic asymmetric synthesis of geminal-dicarboxylates.Chemical science · 2018Article
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3 authors.
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Abstract
The enantioselective N-alkylation of indole and its derivatives with aldimines is efficiently catalyzed by a zinc-ProPhenol dinuclear complex under mild conditions to afford N-alkylated indole derivatives in good yield (up to 86 %) and excellent enantiomeric ratio (up to 99.5:0.5 e.r.). This method tolerates a wide array of indoles, as well as pyrrole and carbazole, to afford the corresponding N-alkylation products. The reaction can be run on a gram scale with reduced catalyst loading without impacting the efficiency. The chiral aminals were further elaborated into various chiral polyheterocyclic derivatives. The surprising stability of the chiral N-alkylation products will open new windows for asymmetric catalysis and medicinal chemistry.
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