Cargando…

The vinylogous Catellani reaction: a combined computational and experimental study

In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed...

Descripción completa

Detalles Bibliográficos
Autores principales:	Yamamoto, Y., Murayama, T., Jiang, J., Yasui, T., Shibuya, M.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Royal Society of Chemistry 2017
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5885779/ https://www.ncbi.nlm.nih.gov/pubmed/29675164 http://dx.doi.org/10.1039/c7sc04265e

Ejemplares similares

Total Synthesis of (+)-Linoxepin by Utilizing the Catellani Reaction**
por: Weinstabl, Harald, et al.
Publicado: (2013)

Catalytic vinylogous cross-coupling reactions of rhenium vinylcarbenoids
por: Chen, Ji, et al.
Publicado: (2018)

Homogeneous and Gas–Liquid Catellani‐Type Reaction Enabled by Continuous‐Flow Chemistry
por: Casnati, Alessandra, et al.
Publicado: (2018)

Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction
por: Wang, Jianchun, et al.
Publicado: (2019)

Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins
por: Sarkar, Rahul, et al.
Publicado: (2018)

Enantioselective vinylogous-Mukaiyama-type dearomatisation by anion-binding catalysis
por: Kaur, Kirandeep, et al.
Publicado: (2021)

Regioselective α-addition of vinylogous α-ketoester enolate in organocatalytic asymmetric Michael reactions: enantioselective synthesis of Rauhut–Currier type products
por: Weng, Zhibing, et al.
Publicado: (2022)

Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones
por: Cui, Jin, et al.
Publicado: (2020)

Asymmetric Friedel−Crafts reaction of unsaturated carbonyl-tethered heteroarenes via vinylogous activation of Pd(0)-π-Lewis base catalysis
por: Jiang, Bo, et al.
Publicado: (2023)

Vinylogous Nitro-Haloform Reaction Enables Aromatic Amination
por: Monasterolo, Claudio, et al.
Publicado: (2022)

Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
por: Richardson, Alistair D., et al.
Publicado: (2022)

Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones
por: Crotti, Simone, et al.
Publicado: (2018)

A convenient method for synthesis of terpyridines via a cooperative vinylogous anomeric based oxidation
por: Karimi, Fatemeh, et al.
Publicado: (2020)

Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
por: Li, Yi, et al.
Publicado: (2022)

Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
por: Yu, Xiaotan, et al.
Publicado: (2023)

Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
por: Hoppmann, Leon, et al.
Publicado: (2021)

Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone
por: Yue, Wen-Jun, et al.
Publicado: (2019)

Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
por: Cordes, Martin, et al.
Publicado: (2019)

Effects of solvents on the DACBO-catalyzed vinylogous Henry reaction of isatin with 3,5-dimethyl-4-nitroisoxazole “on-water” and in solution from QM/MM MC simulations
por: Yang, Lian, et al.
Publicado: (2019)

Catalytic Diastereo- and Enantioselective Vinylogous Mannich Reaction of Alkylidenepyrazolones to Isatin-Derived Ketimines
por: Carceller-Ferrer, Laura, et al.
Publicado: (2021)

Computational exploration of copper catalyzed vinylogous aerobic oxidation of unsaturated compounds
por: Wang, Ting, et al.
Publicado: (2021)

Photoredox-Catalyzed Giese Reactions: Decarboxylative Additions to Cyclic Vinylogous Amides and Esters
por: Dykstra, Kevin, et al.
Publicado: (2022)

A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols
por: Hou, Xufeng, et al.
Publicado: (2016)

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis
por: Hunter, Roger, et al.
Publicado: (2007)

Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts
por: Li, Dan, et al.
Publicado: (2020)

Site-Selective, Photocatalytic Vinylogous Amidation of Enones
por: Szabó, Kitti Franciska, et al.
Publicado: (2022)

A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
por: David, Jonathan G., et al.
Publicado: (2014)

A convenient catalytic method for preparation of new tetrahydropyrido[2,3-d]pyrimidines via a cooperative vinylogous anomeric based oxidation
por: Sepehrmansourie, Hassan, et al.
Publicado: (2022)

Chemical control of the viscoelastic properties of vinylogous urethane vitrimers
por: Denissen, Wim, et al.
Publicado: (2017)

Acidic tributyl phosphonium-based ionic liquid: an efficient catalyst for preparation of diverse pyridine systems via a cooperative vinylogous anomeric-based oxidation
por: Jalali-Mola, Sepideh, et al.
Publicado: (2022)

A combined experimental and computational study on the reaction of fluoroarenes with Mg–Mg, Mg–Zn, Mg–Al and Al–Zn bonds
por: Bakewell, Clare, et al.
Publicado: (2018)

Uncatalyzed conjugate addition of organozinc halides to enones in DME: a combined experimental/computational study on the role of the solvent and the reaction mechanism
por: Casotti, Gianluca, et al.
Publicado: (2019)

Synthesis of new pyridines with sulfonamide moiety via a cooperative vinylogous anomeric-based oxidation mechanism in the presence of a novel quinoline-based dendrimer-like ionic liquid
por: Torabi, Morteza, et al.
Publicado: (2021)

Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones
por: Carceller-Ferrer, Laura, et al.
Publicado: (2022)

An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
por: Philipps, Arne R., et al.
Publicado: (2015)

Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
por: Ahlburg, Nils L., et al.
Publicado: (2022)

Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study
por: Franzoni, Ivan, et al.
Publicado: (2017)

Experimental and computational insights into the mechanism of the copper(i)-catalysed sulfonylative Suzuki–Miyaura reaction
por: Hall, Callum G. J., et al.
Publicado: (2023)

Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds – a combined experimental and mechanistic study
por: Li, Fang, et al.
Publicado: (2021)

Synthesis and Evaluation of N-Diaminophosphoryl Aminothioureas as Bifunctional Catalysts for Vinylogous Aldol Reactions of Isatins and 2(3H)-Furanones
por: D. V., Hrishikesh, et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_p71ieqb228eb74k5v681t05313