Base‐Catalysed (4+2)‐Annulation Between 2‐Nitrobenzofurans and N‐Alkoxyacrylamides: Synthesis of [3,2‐b]Benzofuropyridinones

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(30)

Опубликована: Июль 6, 2022

Abstract An efficient protocol for base‐catalysed (4+2) annulation between 2‐nitrobenzofuran and N ‐alkoxyacrylamide was developed. The corresponding 1‐alkoxy‐3,4‐dihydrobenzofuro[3,2‐ b ]pyridin‐2(1 H )‐ones were obtained in high to excellent yields by organic base catalysis. In addition, a dearomative nitrotetrahydrobenzofuro[3,2‐ ]pyridin‐2(3 also the presence of an inorganic base. advantages this methodology include easily accessible starting materials, simple operational procedures, broad substrate scope, synthetically useful at milder reaction conditions.

Язык: Английский

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Copper-Catalyzed Asymmetric Dearomative [3+2] Cycloaddition of Nitroheteroarenes with Azomethines

Molecules, Год журнала: 2023, Номер 28(6), С. 2765 - 2765

Опубликована: Март 19, 2023

Catalytic asymmetric dearomative [3+2] cycloaddition of α-imino γ-lactones with either 3-nitroindoles or 2-nitrobenzofurans by using a chiral copper complex as the catalyst was developed. A wide range structurally diverse polyheterocyclic compounds containing spirocyclic-fused butyrolactone-pyrrolidine-indoline and butyrolactone-pyrrolidine-dihydrobenzofuran skeletons could be smoothly obtained excellent results (>99:1 dr 98% ee). The potential synthetic applications this methodology were also demonstrated scale-up experiment transformations one product. This method is characterized high induction, functional group tolerance scalability, attractive product diversification.

Язык: Английский

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Transition Metal‐Catalyzed Enantioselective Synthesis of Chiral Five‐ and Six‐Membered Benzo O‐heterocycles

The Chemical Record, Год журнала: 2023, Номер 23(11)

Опубликована: Июль 4, 2023

Enantiomerically enriched five- and six-membered benzo oxygen heterocycles are privileged architectures in functional organic molecules. Over the last several years, many effective methods have been established to access these compounds. However, comprehensive documents cover updated methodologies still highly demand. In this review, recent transition metal catalyzed transformations lead chiral presented. The mechanism chirality transfer or control processes also discussed details.

Язык: Английский

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Dinuclear Zinc Catalyzed [3+2] Annulation of Benzylideneindolinones Access to CF₃‐Containing 2,3‐Pyrrolidinyl Dispirooxindoles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 3088 - 3093

Опубликована: Авг. 9, 2023

Abstract This report has realized the catalytic asymmetric [3+2] annulation of benzylideneindolinones with CF 3 ‐containing isatin‐derived azomethine ylides for first time, in which organocatalysis failed. In presence dinuclear zinc catalysts, a series functionalized 2,3‐pyrrolidinyl dispirooxindoles have been synthesized good yields excellent stereoselectivity under mild reaction conditions. protocol can be run on gram scale and possible mechanism is proposed.

Язык: Английский

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Zn(ii)-catalyzed asymmetric [3 + 2] cycloaddition of acyclic enones with azomethine ylides

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(35), С. 7148 - 7153

Опубликована: Янв. 1, 2024

The ZN( ii )/UCD-Imphanol-catalyzed [3 + 2] asymmetric cycloaddition of acyclic enones and azomethine ylides has been reported. Moderate to high yields (up 94%) with excellent endo / exo selectivities (99 : 1) up 96.5 3.5 er were obtained.

Язык: Английский

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Pd-Catalyzed Intramolecular Dearomative [4 + 2] Cycloaddition of Naphthalenes with Arylalkynes

Organic Letters, Год журнала: 2023, Номер 25(45), С. 8139 - 8144

Опубликована: Ноя. 7, 2023

A Pd-catalyzed intramolecular dearomative [4 + 2] cycloaddition reaction of naphthalenes with arylalkynes is developed. The protocol provides a straightforward method to access range polycyclic dihydronaphthalenes containing two vicinal all-carbon stereocenters in moderate yields under mild conditions an air atmosphere. deuterium labeling experiment suggests pathway involving electrophilic dearomatization followed by Friedel–Crafts cyclization. Several synthetic transformations the product were conducted demonstrate utility this reaction.

Язык: Английский

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Synthesis of Chiral Spiro[oxindole-3,2′-pyrrolidine] Derivatives Integrated with Spiro Indane-1,3-dione and Trifluoromethyl Group Pharmacophores via Organocatalyzed Asymmetric [3+2] Annulation

Synthesis, Год журнала: 2022, Номер 55(09), С. 1427 - 1440

Опубликована: Дек. 6, 2022

Abstract A mild and efficient organocatalyzed [3+2] cycloaddition of isatin-derived ketimines 2-ylideneindane-1,3-diones has been realized. The resulting spiro[oxindole-3,2′-pyrrolidine]s bearing both a spiro indane-1,3-dione motif trifluoromethyl group were obtained in high yields with good diastereo- enantioselectivities.

Язык: Английский

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A base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins: A simple and direct synthesis of dihydrofurobenzofuran-coumarins

Tetrahedron, Год журнала: 2023, Номер 140, С. 133487 - 133487

Опубликована: Май 27, 2023

Язык: Английский

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Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Cyclopentendiones: Access to Functional Cyclopentanediones Bearing an All‐carbon Quaternary Stereocenter

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(18)

Опубликована: Авг. 1, 2023

The success in the identification of two enantioisomeric surfaces electrophiles by dinuclear zinc catalysts is disclosed. This protocol realizes a zinc-cocatalyzed desymmetrization cyclopentendiones using α-hydroxy aryl ketones as nucleophiles through Michael addition reaction. Under mild conditions, series functional cyclopentanediones bearing multiple stereogenic centers including an all-carbon quaternary stereocenter, were obtained moderate to good yields with excellent stereoselectivities.

Язык: Английский

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Copper-Catalyzed Asymmetric [3 + 2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines to Access Three Classes of Polyfunctionalized Spiro-Pyrrolidine–Oxindole Motifs

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7376 - 7381

Опубликована: Авг. 22, 2024

A facile copper-catalyzed [3 + 2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with various electron-deficient alkenes to access structurally polyfunctionalized spiro-pyrrolidine–oxindole motifs has been developed. Under the catalytic system, could be utilized react a series exocyclic alkenes, including 2-acylamino acrylates, 3-methylene-β-lactams, and sterically hindered cycloalkenes represented by cyclobutenone, obtain variety densely functionalized spiro-pyrrolidine frameworks bearing an α-amino acid ester, β-lactam, cyclobutanone, respectively, in generally good yields excellent diastereo- enantioselectivities.

Язык: Английский

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