ArticleJournal of the American Chemical Society2019
Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates: Toward Bisconjugation and Macrocyclization.Organic letters · 2025Article
- 3-Nitroindoles Serving asMolecules (Basel, Switzerland) · 2023Article
- Enantioselective synthesis of N-alkylindoles enabled by nickel-catalyzed C-C coupling.Nature communications · 2022Article
- Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles.Organic letters · 2022Article
- Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.Journal of the American Chemical Society · 2021Article
- Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.Journal of the American Chemical Society · 2020Article
- Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-Organic letters · 2020Article
- Enantioselective Synthesis of Alkyl Allyl Ethers via Palladium-Catalyzed Redox-Relay Heck Alkenylation ofIsrael journal of chemistry · 2020Article
- Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy.Advanced synthesis & catalysis · 2020Article
- Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate.Nature communications · 2020Article
- Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
- Erratum issued
Authors and funding
4 authors.
Funding
Abstract
The development of an intermolecular and enantioselective aza-Wacker reaction is described. Using indoles as the N-source and a selection of alkenols as the coupling partners selective β-hydride elimination toward the alcohol was achieved. This strategy preserves the newly formed stereocenter by preventing the formation of traditionally observed enamine products. Allylic and homoallylic alcohols with a variety of functional groups are compatible with the reaction in high enantioselectivity. Isotopic-labeling experiments support a syn amino-palladation mechanism for this new class of aza-Wacker reactions.
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