Cargando…

Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization

[Image: see text] Here we report the oxidative umpolung of 2,3-disubstituted indoles toward enantioselective dearomative aza-spirocyclization to give the corresponding spiroindolenines using chiral quaternary ammonium hypoiodite catalysis. Mechanistic studies revealed the umpolung reactivity of C3 o...

Descripción completa

Detalles Bibliográficos
Autores principales:	Tanaka, Hiroki, Ukegawa, Naoya, Uyanik, Muhammet, Ishihara, Kazuaki
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2022
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8991020/ https://www.ncbi.nlm.nih.gov/pubmed/35319875 http://dx.doi.org/10.1021/jacs.2c01852

Ejemplares similares

IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone(®)
por: Uyanik, Muhammet, et al.
Publicado: (2012)

Biocatalytic site- and enantioselective oxidative dearomatization of phenols
por: Dockrey, Summer A. Baker, et al.
Publicado: (2017)

Enantioselective N-heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums
por: Flanigan, Darrin M., et al.
Publicado: (2017)

Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides
por: Li, Xingguang, et al.
Publicado: (2021)

Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(ii) complex
por: Yao, Lu, et al.
Publicado: (2019)

Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines
por: Chao, Junli, et al.
Publicado: (2022)

Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines
por: Greßies, Steffen, et al.
Publicado: (2023)

A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation
por: Wu, Zijun, et al.
Publicado: (2018)

Candida albicans susceptibility to lactoperoxidase-generated hypoiodite
por: Ahariz, Mohamed, et al.
Publicado: (2010)

Enantioselective dearomatization reactions of heteroarenes by anion-binding organocatalysis
por: Aleksiev, Martin, et al.
Publicado: (2023)

Carbonyl Hypoiodites as Extremely Strong Halogen Bond Donors
por: Yu, Shilin, et al.
Publicado: (2021)

Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters
por: Choudhury, Abhijnan Ray, et al.
Publicado: (2017)

Highly enantioselective Rh-catalyzed asymmetric reductive dearomatization of multi-nitrogen polycyclic pyrazolo[1,5-a]pyrimidines
por: Xie, Chaochao, et al.
Publicado: (2023)

Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles
por: Liang, Ren-Xiao, et al.
Publicado: (2019)

Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO(2)
por: Yan, Si-Shun, et al.
Publicado: (2018)

N,N‐Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion‐Binding Catalysis
por: Gómez‐Martínez, Melania, et al.
Publicado: (2021)

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation
por: Rossi‐Ashton, James A., et al.
Publicado: (2020)

Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation
por: Boyd, Derek R., et al.
Publicado: (2022)

Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols
por: Wu, Wen-Ting, et al.
Publicado: (2016)

Helical Multi‐Coordination Anion‐Binding Catalysts for the Highly Enantioselective Dearomatization of Pyrylium Derivatives
por: Fischer, Theresa, et al.
Publicado: (2018)

Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates
por: Ray Choudhury, Abhijnan, et al.
Publicado: (2016)

Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
por: Yeung, Charles S., et al.
Publicado: (2014)

Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
por: Zhang, Pan, et al.
Publicado: (2019)

Susceptibility of influenza viruses to hypothiocyanite and hypoiodite produced by lactoperoxidase in a cell-free system
por: Patel, Urmi, et al.
Publicado: (2018)

An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
por: Bauer, Adriano, et al.
Publicado: (2020)

Direct dehydrogenative alkyl Heck-couplings of vinylarenes with umpolung aldehydes catalyzed by nickel
por: Lv, Leiyang, et al.
Publicado: (2019)

Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO(2)
por: Cao, Guang-Mei, et al.
Publicado: (2021)

Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles
por: Liu, Kai, et al.
Publicado: (2017)

Enantioselective aromatic Claisen rearrangement of allyl 2-naphthyl ethers catalyzed by π–Cu(ii) complexes
por: Yao, Lu, et al.
Publicado: (2023)

Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
por: Seoane, Andrés, et al.
Publicado: (2014)

Positioning-Group-Enabled Biocatalytic Oxidative Dearomatization
por: Dockrey, Summer A. Baker, et al.
Publicado: (2019)

The inverted ketene synthon: a double umpolung approach to enantioselective β(2,3)-amino amide synthesis
por: Vishe, Mahesh, et al.
Publicado: (2018)

Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand
por: Huang, Shuai, et al.
Publicado: (2021)

Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation
por: Zhang, Yueteng, et al.
Publicado: (2021)

Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
por: Zhang, Xiao, et al.
Publicado: (2015)

Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids
por: Wang, Guo-Peng, et al.
Publicado: (2017)

N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
por: Ramarao, Jakkula, et al.
Publicado: (2022)

sSPhos: A General Ligand for Enantioselective Arylative Phenol Dearomatization via Electrostatically-Directed Palladium Catalysis
por: Kadarauch, Max, et al.
Publicado: (2023)

Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence
por: Xia, Zi-Lei, et al.
Publicado: (2019)

Metal-free borylative dearomatization of indoles: exploring the divergent reactivity of aminoborane C–H borylation catalysts
por: Jayaraman, Arumugam, et al.
Publicado: (2018)

Cannot write session to /tmp/vufind_sessions/sess_tg7t7a50v0sqm3fjodveil20a8