ArticleCommunications chemistry2020
Nickel-catalyzed enantioselective reductive carbo-acylation of alkenes.
Article in Communications chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 68 citations in OpenAlex.
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes.Journal of the American Chemical Society · 2023Article
- Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams.Nature communications · 2022Article
- Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes.Molecules (Basel, Switzerland) · 2022Article
- Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes.Angewandte Chemie (International ed. in English) · 2022Article
- Nickel-catalysed cross-electrophile coupling of aryl bromides and primary alkyl bromides.RSC advances · 2022Article
- Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes.ACS catalysis · 2021Article
- Catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides via selective C-F bond activation.Nature communications · 2021Article
- Three-Component Ni-Catalyzed Silylacylation of Alkenes.ACS catalysis · 2021Article
- Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.ACS catalysis · 2020Article
- Nickel-Catalyzed Dicarbofunctionalization of Alkenes.ACS catalysis · 2020Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Recently, transition-metal-catalyzed asymmetric dicarbofunctionalization of tethered alkenes has emerged as a powerful method for construction of chiral cyclic carbo- and heterocycles. However, all these reactions rely on facially selective arylmetalation of the pendant olefinic unit. Here, we successfully apply acylnickelation as the enantiodetermining step in the asymmetric nickel-catalyzed reductive carbo-acylation of aryl carbamic chloride-tethered alkenes with primary and secondary alkyl iodides as well as benzyl chlorides as the coupling partners, using manganese as a reducing agent. By circumventing the use of pre-generated organometallics, this reductive strategy enables the synthesis of diverse enantioenriched oxindoles bearing a quaternary stereogenic center under mild reaction conditions with high tolerance of a broad range of functional moieties.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.