Cargando…

Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2 + 2] cycloaddition: a synthetic and computational study

The enantioselective preparation of a range of perfluoroalkyl-substituted β-lactones through an isothiourea (HyperBTM) catalysed reaction using symmetric anhydrides as ammonium enolate precursors and perfluoroalkylketones (R(F) = CF(3), C(2)F(5), C(4)F(9)) is reported. Following optimisation, high d...

Descripción completa

Detalles Bibliográficos
Autores principales:	Barrios Antúnez, Diego-Javier, Greenhalgh, Mark D., Brueckner, Alexander C., Walden, Daniel M., Elías-Rodríguez, Pilar, Roberts, Patrick, Young, Benjamin G., West, Thomas H., Slawin, Alexandra M. Z., Ha-Yeon Cheong, Paul, Smith, Andrew D.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Royal Society of Chemistry 2019
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6585878/ https://www.ncbi.nlm.nih.gov/pubmed/31360423 http://dx.doi.org/10.1039/c9sc00390h

Ejemplares similares

Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
por: Zhou, Wei, et al.
Publicado: (2017)

6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
por: Neyyappadath, Rifahath M., et al.
Publicado: (2017)

Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study
por: West, Thomas H., et al.
Publicado: (2017)

Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light
por: Balletti, Matteo, et al.
Publicado: (2023)

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis
por: Matviitsuk, Anastassia, et al.
Publicado: (2017)

A Desilylative Approach to Alkyl Substituted C(1)‐Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions
por: Wang, Yihong, et al.
Publicado: (2022)

Dynamic Catalytic Highly Enantioselective 1,3‐Dipolar Cycloadditions
por: Yildirim, Okan, et al.
Publicado: (2021)

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
por: Zhang, Shuyue, et al.
Publicado: (2020)

Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones
por: Wang, Yihong, et al.
Publicado: (2023)

Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β‐Unsaturated Esters
por: Bitai, Jacqueline, et al.
Publicado: (2022)

Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters
por: Woźniak, Łukasz, et al.
Publicado: (2015)

Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented Synthesis
por: Narayan, Rishikesh, et al.
Publicado: (2014)

Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and Secondary γ-C–H Bonds
por: Call, Arnau, et al.
Publicado: (2023)

Mechanism and origins of selectivity in the enantioselective oxa-Pictet–Spengler reaction: a cooperative catalytic complex from a hydrogen bond donor and chiral phosphoric acid
por: Maskeri, Mark A., et al.
Publicado: (2020)

Gold(I)-catalyzed enantioselective cycloaddition reactions
por: López, Fernando, et al.
Publicado: (2013)

Enantioselective Nozaki–Hiyama–Kishi allylation-lactonization for the syntheses of 3-substituted phthalides
por: Kumbhar, Sharad V., et al.
Publicado: (2018)

Concerted [4 + 2] and Stepwise (2 + 2) Cycloadditions of Tetrafluoroethylene with Butadiene: DFT and DLPNO-UCCSD(T) Explorations
por: Svatunek, Dennis, et al.
Publicado: (2020)

Crossed Regio‐ and Enantioselective Iron‐Catalyzed [4+2]‐Cycloadditions of Unactivated Dienes
por: Braconi, Elena, et al.
Publicado: (2021)

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
por: Davies, Alyn T, et al.
Publicado: (2020)

Neutral chiral cyclopentadienyl Ru(ii)Cl catalysts enable enantioselective [2+2]-cycloadditions
por: Kossler, D., et al.
Publicado: (2017)

Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
por: Sendra, Jana, et al.
Publicado: (2021)

Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids
por: Kowalska, Ewelina, et al.
Publicado: (2022)

Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-C(2) Symmetric Digold Catalysts
por: García-Morales, Cristina, et al.
Publicado: (2017)

Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
por: Laviós, Adrian, et al.
Publicado: (2022)

An endo‐Directing‐Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes
por: Sokolova, Olga O., et al.
Publicado: (2022)

Chemodivergence in Pd-catalyzed desymmetrization of allenes: enantioselective [4+3] cycloaddition, desymmetric allenylic substitution and enynylation
por: Luo, Pengfei, et al.
Publicado: (2023)

Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines
por: McLean, Liam A., et al.
Publicado: (2022)

Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles
por: Robinson, Emily R. T., et al.
Publicado: (2016)

Nonequilibrium Dynamics of Proton-Coupled Electron Transfer in Proton Wires: Concerted but Asynchronous Mechanisms
por: Goings, Joshua J., et al.
Publicado: (2020)

Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization
por: Lu, Licheng, et al.
Publicado: (2023)

Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine
por: Payne, Jenna L., et al.
Publicado: (2022)

Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates
por: Flesch, Kaylin N., et al.
Publicado: (2023)

Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis
por: Greenhalgh, Mark D., et al.
Publicado: (2018)

Enantioselective Cycloaddition of Münchnones onto [60]Fullerene: Organocatalysis versus Metal Catalysis
por: Marco-Martínez, Juan, et al.
Publicado: (2014)

Chemodivergent, Regio‐ and Enantioselective Cycloaddition Reactions between 1,3‐Dienes and Alkynes
por: Singh, Dipshi, et al.
Publicado: (2023)

Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
por: Nishiura, Yuji, et al.
Publicado: (2023)

Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
por: Liu, Ren-Rong, et al.
Publicado: (2017)

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts
por: McLaughlin, Calum, et al.
Publicado: (2021)

Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
por: Ngamnithiporn, Aurapat, et al.
Publicado: (2018)

Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction
por: Steurer, Marianne, et al.
Publicado: (2012)

Cannot write session to /tmp/vufind_sessions/sess_ph433voqr966fv385tqoghlkq5