☆ 4.7 Article

Palladium-catalyzed asymmetric (4+3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles

ORGANIC CHEMISTRY FRONTIERS (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Review Chemistry, Physical

Advances in Palladium-Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

Yong You et al.

Summary: Palladium-catalyzed decarboxylative cycloadditions have emerged as highly efficient methods for constructing structurally diverse carbo- and heterocycles due to their ability to form multiple carbon-carbon or carbon-heteroatom bonds in a single step. This review discusses the achievements and synthetic applications of these reactions involving cyclic carbonates, carbamates, and lactones for accessing oxacyclo-, azacyclo-, and carbocyclic compounds. Mechanistic insights and the challenges and opportunities in this field are also addressed.

CHEMCATCHEM (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Advances in Lewis Base-Catalysed Chemo-, Diastereo- and Enantiodivergent Reactions of Electron-deficient Olefins and Alkynes

Yinggao Meng et al.

Summary: Lewis base catalysis provides powerful synthetic strategies for the selective construction of carbon-carbon and carbon-heteroatom bonds. The nucleophilicity and steric hindrance of Lewis base catalyst often plays a major role in catalytic reactivity and selectivity in the reaction. Tremendous progress has been made in the divergent construction of valuable motifs under Lewis base catalysis in the past decades.

CHEMICAL RECORD (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates

Manman Song et al.

Summary: This review provides a comprehensive and updated summary of the use of tertiary amine Lewis bases as catalysts for annulation reactions of allenoates. The review highlights diverse reactivities, chemoselectivities, and detailed reaction mechanisms.

CHINESE CHEMICAL LETTERS (2022)

添加到收藏夹

Article Chemistry, Applied

Palladium-Catalyzed [4+2] Cycloaddition of Hydroxy-Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans

Jiaqing Xu et al.

Summary: A palladium-catalyzed [4+2] cycloaddition reaction has been developed for the efficient synthesis of tetrahydropyran derivatives with good selectivity.

ADVANCED SYNTHESIS & CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Medicinal

Organocatalyzed asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans and N-2,2,2-trifluoroethylisatin ketimines

Xiao-Jian Zhou et al.

Summary: A readily available chiral cyclohexanediamine-derived bifunctional tertiary amine-squaramide catalyst has been developed for the asymmetric dearomative 1,3-dipolar cycloaddition reaction. The catalyst shows high efficiency, mild reaction conditions, excellent enantioselectivity, wide functional group tolerance, great potential for scale-up synthesis, and attractive product diversification.

CHIRALITY (2022)

添加到收藏夹

Article Chemistry, Organic

Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines Enables the Desymmetrization of N-Arylmaleimides: Access to Enantioenriched F3C-Containing Octahydropyrrolo[3,4-c]pyrroles

Zhen-Hua Wang et al.

Summary: In this study, the enantioselective desymmetrization of N-arylmaleimides was achieved using a Cu(OTf)(2)/chiral ferrocenyl P,N-ligand complex as a catalyst, through the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (<= 99% yield, >20:1 dr, and 99% ee).

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Umpolung of N-2,2,2-Trifluoroethylisatin Ketimines for the Enantioselective 1,3-Dipolar Cycloaddition with Benzo[b]thiophene Sulfones

Wei-Cheng Yuan et al.

Summary: A copper-catalyzed reaction of N-2,2,2-trifluoroethylisatin ketimines with benzo[b]thiophene sulfones was developed for the enantioselective 1,3-dipolar cycloaddition. The reaction afforded pentacyclic spirooxindoles containing pyrrolidine and benzo[b]sulfolane subunits in high efficiency and with excellent selectivity under mild conditions.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

Lu Wang et al.

Summary: 3-CF3S substituted thioflavones and benzothiophenes were achieved through reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, promoted by persulfate. This protocol shows good functional group tolerance and high yields. Mechanistic studies indicate a classic two-step radical process involving addition of CF3S radical to triple bond and cyclization with SMe moiety.

CHINESE CHEMICAL LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Formal [5+3] Cycloaddition between Isatin-Based α-(Trifluoromethyl)imine Ylides and Vinyloxiranes: Diastereoselective Access to Medium-Heterocycle-Fused Spirooxindoles

Hong-Wu Zhao et al.

Summary: The formal [5+3] cycloaddition between isatin-based alpha-(trifluoromethyl)imines and vinyloxiranes proceeded readily in the presence of Pd-2(dba)(3)center dot CHCl3(2.5 mol%), PPh3(10 mol%), and 60% NaH (1.5 equiv) in 1,2-DCE at 40 celcius, affording cis-configured medium-heterocycle-fused spirooxindoles in reasonable chemical yields with >20:1 dr. The relative stereochemical configuration of the products was determined by X-ray diffraction analysis.

SYNLETT (2021)

添加到收藏夹

Article Chemistry, Organic

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

Jian-Qiang Zhao et al.

Summary: An enantioselective dearomative 1,3-dipolar cyclo-addition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides was achieved using a bifunctional hydrogen-bonding thiourea catalyst, resulting in excellent yields and enantioselectivity. The chiral selectivity could be reversed by a bifunctional hydrogen-bonding squaramide catalyst with the same chiral source. DFT calculations provided insights into the stereochemistry and enantioselectivity reversal observed in the reaction.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Asymmetric [4+3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis

Zhi Chen et al.

Summary: Asymmetric [4 + 3] annulations were successfully achieved using isatin-derived Morita-Baylis-Hillman carbonates and two types of vinyl carbonates synergistically catalyzed by tertiary amines and transition metals. This method allows for the construction of a variety of oxepane frameworks with high stereocontrol, and all four diastereomers for products bearing vicinal stereocenters can be accessed by tuning the tertiary amine and metal catalysts.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Six-Membered Spiro Azacyclic Oxindole Derivatives via a One-Pot Process of Umpolung Allylation/Aza-Prins Cyclization

Woo Cheol Jang et al.

Summary: This study describes an unprecedented synthetic approach involving umpolung allylation/aza-Prins cyclization of N-2,2,2-trifluoroethylisatin ketimines, leading to the formation of six-membered spiro azacyclic oxindole derivatives.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Diastereodivergent synthesis of fully disubstituted spiro[indoline-3,2′-pyrrolidin]-2-ones via tuneable Lewis base/Bronsted base-promoted (3+2) cycloadditions

Ke Li et al.

Summary: In this study, a diastereodivergent synthesis of fully disubstituted spiro[indoline-3,2'-pyrrolidin]-2-ones was achieved through base-promoted (3 + 2) cycloadditions. Catalysts were found to exert full control over the configuration of stereocenters. Different diastereoisomers of spiro[indoline-3,2'-pyrrolidin]-2-ones were obtained with good yields by using different types of bases (Lewis base PCy3 and Bronsted base K2CO3), demonstrating the influence of the catalysts on the stereoselectivity of the reaction. ESI-MS experiments confirmed the presence of key zwitterionic intermediates.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Editorial Material Multidisciplinary Sciences

Enantioselective trapping of palladium-stabilized oxo-1,4-dipoles with photochemically generated ketenes

Miao-Miao Li et al.

SCIENCE BULLETIN (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Spirotetrahydrofuran Oxindoles via Palladium-Catalyzed [4+1] Cycloaddition of Diphenyl 2-Oxoindolin-3-yl Phosphates and 2-Methylidenetrimethylene Carbonate

Yuming Li et al.

Summary: A novel palladium-catalyzed [4 + 1] cycloaddition reaction has been developed for the synthesis of spirotetrahydrofuran oxindoles. This method utilizes diphenyl 2-oxoindolin-3-yl phosphates and 2-methylidenetrimethylene carbonate as reactants to provide the desired compounds in good to excellent yields at room temperature, offering a new strategy for the construction of spirooxindole derivatives with unique three-dimensional structures.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

Shang-Shi Zhang et al.

Summary: A novel rhodium(III)-catalyzed C-H allylation reaction has been developed using 2-methylidenetrimethylene carbonate as an efficient allylic source, resulting in the synthesis of various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields. Five different directing groups, including oxime, N-nitroso, purine, pyridine, and pyrimidine, were found to be compatible in this reaction.

ORGANIC LETTERS (2021)

添加到收藏夹

Review Chemistry, Organic

Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines

Zhongwen Sun et al.

Summary: This article reviews the research progress of catalytic asymmetric reactions involving trifluoroethylketimine in recent five years and prospects the future development in this field.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of novel pyridinium 1,5-zwitterions and their reactivity with isatin-based α-(trifluoromethyl)imines: a sulfur-controlled domino reaction

Gaoting Zhang et al.

Summary: A new stable pyridinium 1,5-zwitterion was isolated, and its stability was attributed to the polarization effect on the exocyclic double bond according to DFT calculations. The reaction of pyridinium 1,5-zwitterion with isatin-derived alpha-(trifluoromethyl)imine was temperature-dependent, with umpolung [4 + 3] annulation occurring at 20 degrees C. Interestingly, the presence of a sulfur atom changed the reaction mode from umpolung [4 + 3] to classical [3 + 2] annulation.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Remote regioselective organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethyl isatin ketimines with cyclic 2,4-dienones

Chuncheng Zou et al.

CHINESE CHEMICAL LETTERS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Advances in the Construction of Trifluoromethyl-Containing Spirooxindoles through Cycloaddition Reactions

Hou-Ze Gui et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric [4+2] Cycloaddition of 2-Methylidenetrimethylene Carbonate with Alkenes: Access to Chiral Tetrahydropyran-Fused Spirocyclic Scaffolds

Biming Mao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Organic

Bronsted Base and Lewis Acid Cooperatively Catalyzed Asymmetric exo′-Selective [3+2] Cycloaddition of Trifluoromethylated Azomethine Ylides and Methyleneindolinones

Yang Yi et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Review Chemistry, Applied

Recent Advances in Organocatalyst-Mediated Benzannulation Reactions

Lulu Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Physical

Modular Synthesis of Medium-Sized Fluorinated and Nonfluorinated Heterocyclic Lactones by Sequential CN-Bond-Cleaving Ring Expansion under Pd Catalysis

Hiroto Uno et al.

ACS CATALYSIS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in phosphine catalysis involving γ-substituted allenoates

Er-Qing Li et al.

CHEMICAL COMMUNICATIONS (2020)

添加到收藏夹

Article Chemistry, Organic

Catalytic Asymmetric Synthesis of α-Trifluoromethyl Homoallylic Amines via Umpolung Allylation/2-Aza-Cope Rearrangement: Stereoselectivity and Mechanistic Insight

Li-Min Shi et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Organic

Palladium-Catalyzed Diastereoselective Formal [5+3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring

Ben Niu et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Applied

Formal [5+3] Cycloaddition of Vinylethylene Carbonates with Isatin-Based α-(Trifluoromethyl)imines for Diastereoselective Synthesis of Medium-Heterocycle-Fused Spirooxindoles

Hong-Wu Zhao et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

添加到收藏夹

Article Chemistry, Organic

Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes

Xin-Yue Gao et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Organic

Highly efficient enantioselective synthesis of bispiro[benzofuran-oxindole-pyrrolidine]s through organocatalytic cycloaddition

Boyu Li et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic Asymmetric [3+2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines with β-Trifluoromethyl Electron Deficient Alkenes: Access to Vicinally Bis(trifluoromethyl)-Substituted 3,2′-Pyrrolidinyl Spirooxindoles

Yong You et al.

ORGANIC LETTERS (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Utilizing Palladium-Stabilized Zwitterions for the Construction of N-Heterocycles

Benjamin D. W. Allen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent catalytic syntheses of trifluoromethylthio-containing organic compounds by transition metals, chiral organocatalysts, and photocatalysts

Yong Guo et al.

CHINESE CHEMICAL LETTERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2′-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction

Mingxia Ma et al.

CHEMICAL COMMUNICATIONS (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Good Partnership between Sulfur and Fluorine: Sulfur-Based Fluorination and Fluoroalkylation Reagents for Organic Synthesis

Chuanfa Ni et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups

Hiromichi Egami et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001-2011)

Jiang Wang et al.

CHEMICAL REVIEWS (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Addition of CF3 across unsaturated moieties: a powerful functionalization tool

Estibaliz Merino et al.

CHEMICAL SOCIETY REVIEWS (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Introduction of Fluorine and Fluorine-Containing Functional Groups

Theresa Liang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates

Ryo Shintani et al.

CHEMICAL COMMUNICATIONS (2011)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids

Rene Smits et al.

CHEMICAL SOCIETY REVIEWS (2008)

添加到收藏夹

Review Multidisciplinary Sciences

Fluorine in pharmaceuticals:: Looking beyond intuition

Klaus Mueller et al.

SCIENCE (2007)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.