Catalytic cascade reactions /

"The development of catalytic versions of cascade reactions has become one of the most active and burgeoning reaction areas in organic synthesis. Covering both organocatalysis and transition-metal catalysis for these reactions, Catalytic Cascade Reactions illustrates the versatility and applica...

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Detalles Bibliográficos
Clasificación:Libro Electrónico
Otros Autores: Xu, Peng-Fei, 1964- (Editor ), Wang, Wei (Associate professor of chemistry) (Editor )
Formato: Electrónico eBook
Idioma:Inglés
Publicado: Hoboken, New Jersey : Wiley, [2013]
Temas:
Organic reaction mechanisms.
Catalysis.
Chemical reactions.
Organic compounds > Synthesis.
Catalysis
Réactions organiques (Chimie) > Mécanismes.
Catalyse.
Composés organiques > Synthèse.
SCIENCE > Chemistry > Organic.
Chemical reactions
Organic compounds > Synthesis
Organic reaction mechanisms
Acceso en línea:Texto completo
Tabla de Contenidos:
  • Catalytic Cascade Reactions
  • Copyright
  • Contents
  • Contributors
  • Preface
  • 1 Amine-Catalyzed Cascade Reactions
  • 1.1 Introduction
  • 1.2 Enamine-Activated Cascade Reactions
  • 1.2.1 Enamine-Enamine Cascades
  • 1.2.1.1 Design of Enamine-Enamine Cascades
  • 1.2.1.2 Examples of Enamine-Enamine and Enamine-Enamine Cyclization Cascades
  • 1.2.1.3 Enamine-Enamine in Three-Component Cascades
  • 1.2.1.4 Enamine-Activated Double a-Functionalization
  • 1.2.1.5 Robinson Annulations
  • 1.2.2 Enamine-Iminium Cascades
  • 1.2.2.1 Design of Enamine-Iminium Cascades
  • 1.2.2.2 Examples of [4 + 2] Reactions with Enamine-Activated Dienes
  • 1.2.2.3 Inverse-Electron-Demand [4 + 2] Reactions with Enamine-Activated Dienophiles
  • 1.2.2.4 Enamine-Iminium-Enamine Cascades
  • 1.2.3 Enamine Catalysis Cyclization
  • 1.2.3.1 Design of Enamine-Cyclization Cascade Reactions
  • 1.2.3.2 Enamine-Intermolecular Addition Cascades
  • 1.2.3.3 Enamine-Intramolecular Addition Cascades
  • 1.2.3.4 Enamine-Intramolecular Aldol Cascades
  • 1.3 Iminium-Initiated Cascade Reactions
  • 1.3.1 Design of Iminium-Enamine Cascade Reactions
  • 1.3.2 Iminium-Activated Diels-Alder Reactions
  • 1.3.3 Iminium-Activated Sequential [4+2] Reactions
  • 1.3.4 Iminium-Activated [3+2] Reactions
  • 1.3.5 Iminium-Activated Sequential [3+2] Reactions
  • 1.3.6 Iminium-Activated [2+1] Reactions
  • 1.3.6.1 Iminium-Activated Cyclopropanations
  • 1.3.6.2 Iminium-Activated Epoxidations
  • 1.3.6.3 Iminium-Activated Aziridinations
  • 1.3.7 Iminium-Activated Multicomponent Reactions
  • 1.3.8 Iminium-Activated [3+3] Reactions
  • 1.3.8.1 Iminium-Activated All-Carbon-Centered [3+3] Reactions
  • 1.3.8.2 Imin ium-Activated Hetero-[3+3] Reactions
  • 1.3.9 Other Iminium-Activated Cascade Reactions
  • 1.4 Cycle-Specific Catalysis Cascades
  • 1.5 Other Strategies
  • 1.6 Summary and Outlook
  • References.
  • 2 Brønsted Acid-Catalyzed Cascade Reactions
  • 2.1 Introduction
  • 2.2 Protonic Acid-Catalyzed Cascade Reactions
  • 2.2.1 Mannich Reaction
  • 2.2.2 Pictect-Spengler Reaction
  • 2.2.3 Biginelli Reaction
  • 2.2.4 Povarov Reaction
  • 2.2.5 Reduction Reaction
  • 2.2.6 1,3-Dipolar Cycloaddition
  • 2.2.7 Darzen Reaction
  • 2.2.8 Acyclic Aminal and Hemiaminal Synthesis
  • 2.2.9 Rearrangement Reaction
  • 2.2.10 a, b -Unsaturated Imine-Involved Cyclization Reaction
  • 2.2.11 Alkylation Reaction
  • 2.2.12 Desymmetrization Reaction
  • 2.2.13 Halocyclization
  • 2.2.14 Redox Reaction
  • 2.2.15 Isocyanide-Involved Multicomponent Reaction
  • 2.2.16 Other Protonic Acid-Catalyzed Cascade Reactions
  • 2.3 Chiral Thiourea (Urea)-Catalyzed Cascade Reactions
  • 2.3.1 Neutral Activation
  • 2.3.1.1 Halolactonization
  • 2.3.1.2 Mannich Reaction
  • 2.3.1.3 Michael-Aldol Reaction
  • 2.3.1.4 Michael-Alkylation Reaction
  • 2.3.1.5 Cyano-Involved Michael-Cyclization Reaction
  • 2.3.1.6 Michael-Hemiketalization (Hemiacetalization) Reaction
  • 2.3.1.7 Michael-Henry Reaction
  • 2.3.1.8 Michael-Michael Reaction
  • 2.3.1.9 Petasis Reaction
  • 2.3.1.10 Sulfur Ylide-Involved Michael-Cyclization Reaction
  • 2.3.1.11 a-Isothiocyanato Imide-Involved Cascade Reaction
  • 2.3.1.12 a-Isocyanide-Involved Cascade Reaction
  • 2.3.2 Anion-Binding Catalysis
  • 2.3.2.1 Pictet-Spengler Reaction
  • 2.3.2.2 Other Iminium Ion-Involved Cascade Reaction
  • 2.3.2.3 Oxocarbenium Ion-Involved Cascade Reaction
  • 2.4 Brønsted Acid and Transition Metal Cooperatively Catalyzed Cascade Reactions
  • 2.4.1 Dual Catalysis
  • 2.4.2 Cascade Catalysis
  • 2.4.2.1 Pd(0)/Brønsted Acid System
  • 2.4.2.2 Ruthenium/Brønsted Acid System
  • 2.4.2.3 Au(I)/Brønsted Acid System
  • 2.4.2.4 Other Binary Catalytic Systems
  • 2.5 Conclusions
  • References.
  • 3 Application of Organocatalytic Cascade Reactions in Natural Product Synthesis and Drug Discovery
  • 3.1 Introduction
  • 3.2 Amine-Catalyzed Cascade Reactions in Natural Product Synthesis
  • 3.2.1 Iminium-Ion-Catalyzed Cascade Reactions in Natural Product Synthesis
  • 3.2.2 Cycle-Specific Cascade Catalysis in Natural Product Synthesis
  • 3.2.2.1 Iminium-Enamine Cycle-Specific Cascade Catalysis
  • 3.2.2.2 Enamine (/Dienamine)-Iminium Cycle-Specific Cascade Catalysis
  • 3.2.2.3 More Complex Cycle-Specific Cascade Catalysis
  • 3.3 Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
  • 3.4 Bifunctional Base/Brønsted Acid-Catalyzed Cascade Reactions in Natural Product Synthesis
  • 3.5 Summary and Outlook
  • References
  • 4 Gold-Catalyzed Cascade Reactions
  • 4.1 Introduction
  • 4.2 Cascade Reactions of Alkynes
  • 4.2.1 Cascade Reactions of Enynes
  • 4.2.1.1 Cascade Reactions of 1,6-Enynes
  • 4.2.1.2 Cascade Reactions of 1,5-Enynes
  • 4.2.1.3 Cascade Reactions of 1,4-Enynes
  • 4.2.1.4 Cascade Reactions of 1,3-Enynes
  • 4.2.1.5 Cascade Reactions of 1,n-Enynes (n> 6)
  • 4.2.2 Cascade Reactions of Propargyl Carboxylates
  • 4.2.3 Cascade Reactions of ortho-Substituted Arylalkynes
  • 4.2.4 Cascade Reactions of Other Alkynes
  • 4.3 Cascade Reactions of Allenes
  • 4.4 Cascade Reactions of Alkenes and Cyclopropenes
  • 4.5 Closing Remarks
  • References
  • 5 Cascade Reactions Catalyzed by Ruthenium, Iron, Iridium, Rhodium, and Copper
  • 5.1 Introduction
  • 5.2 Ruthenium-Catalyzed Transformations
  • 5.3 Iron-Catalyzed Transformations
  • 5.4 Iridium-Catalyzed Transformations
  • 5.5 Rhodium-Catalyzed Transformations
  • 5.6 Copper-Catalyzed Transformations
  • 5.7 Miscellaneous Catalytic Reactions
  • 5.8 Summary
  • References
  • 6 Palladium-Catalyzed Cascade Reactions of Alkenes, Alkynes, and Allenes
  • 6.1 Introduction.
  • 6.2 Cascade Reactions Involving Alkenes
  • 6.2.1 Double Mizoroki-Heck Reaction Cascade
  • 6.2.2 Cascade Heck Reaction/C-H Activation
  • 6.2.3 Cascade Heck Reaction/Reduction/ Cyclization
  • 6.2.4 Cascade Heck Reaction/Carbonylation
  • 6.2.5 Cascade Heck Reaction/ Suzuki Coupling
  • 6.2.6 Cascade Amino-/Oxopalladation/Carbopalladation Reaction
  • 6.3 Cascade Reactions Involving Alkynes
  • 6.3.1 Cascade Heck Reactions
  • 6.3.2 Cascade Heck/Suzuki Coupling
  • 6.3.3 Cationic Palladium(II)-Catalyzed Cascade Reactions
  • 6.3.4 Cascade Heck Reaction/Stille Coupling
  • 6.3.5 Cascade Heck/Sonogashira Coupling
  • 6.3.6 Cascade Sonogashira Coupling-Cyclization
  • 6.3.7 Cascade Heck and C-H Bond Functionalization
  • 6.3.8 Cascade Reactions Initiated by Oxopalladation
  • 6.3.9 Cascade Reactions Initiated by Aminopalladation
  • 6.3.10 Cascade Reactions Initiated by Halopalladation or Acetoxypalladation
  • 6.3.11 Cascade Reactions of 2-(1-Alkynyl)-alk-2-en-1-ones
  • 6.3.12 Cascade Reactions of Propargylic Derivatives
  • 6.4 Cascade Reactions Involving Allenes
  • 6.4.1 Cascade Reactions of Monoallenes
  • 6.4.2 Cross-Coupling Cyclization of Two Different Allenes
  • 6.5 Summary and Outlook
  • Acknowledgments
  • References
  • 7 Use of Transition Metal-Catalyzed Cascade Reactions in Natural Product Synthesis and Drug Discovery
  • 7.1 Introduction
  • 7.2 Palladium-Catalyzed Cascade Reactions in Total Synthesis
  • 7.2.1 Cross-Coupling Reactions
  • 7.2.1.1 Heck Reaction
  • 7.2.1.2 Stille Reaction
  • 7.2.1.3 Suzuki Coupling Reaction
  • 7.2.2 Tsuji-Trost Reaction
  • 7.2.3 Other Palladium-Catalyzed Cascade Reactions in Total Synthesis
  • 7.3 Ruthenium-Catalyzed Cascade Reactions in Total Synthesis
  • 7.4 Gold- and Platinum-Catalyzed Cascade Reactions in Organic Reactions
  • 7.5 Copper- and Rhodium-Catalyzed Cascade Reactions in O rganic Synthesis
  • 7.6 Summary
  • References.
  • 8 Engineering Mono- and Multifunctional Nanocatalysts for Cascade Reactions
  • 8.1 Introduction
  • 8.2 Heterogeneous Monofunctional Nanocatalysts
  • 8.2.1 Metal-Based Monofunctional Nanocatalysts
  • 8.2.2 Metal Oxide-Based Monofunctional Nanocatalysts
  • 8.2.3 Orgamometallic-Based Monofunctional Nanocatalysts
  • 8.2.4 Graphene Oxide-Based Monofunctional Nanocatalysts
  • 8.3 Heterogeneous Multifunctional Nanocatalysts
  • 8.3.1 Acid-Base Combined Multifunctional Nanocatalysts
  • 8.3.2 Metal-Base Combined Multifunctional Nanocatalysts
  • 8.3.3 Organometallic-Base Combined Multifunctional Nanocatalysts
  • 8.3.4 Binary Organometallic-Based Multifunctional Nanocatalysts
  • 8.3.5 Binary Metal-Based Multifunctional Nanocatalysts
  • 8.3.6 Metal-Metal Oxide Combined Multifunctional Nanocatalysts
  • 8.3.7 Organocatalyst-Acid Combined Multifunctional Nanocatalysts
  • 8.3.8 Acid-Base-Metal Combined Multifunctional Nanocatalysts
  • 8.3.9 Triple Enzyme-Based Multifunctional Nanocatalysts
  • 8.4 Conclusions and Perspectives
  • References
  • 9 Multiple-Catalyst-Promoted Cascade Reactions
  • 9.1 Introduction
  • 9.2 Multiple Metal Catalyst-Promoted Cascade Reactions
  • 9.2.1 Catalytic Systems Involving Palladium
  • 9.2.2 Catalytic Systems Involving Other Metals
  • 9.3 Multiple Organocatalyst-Promoted Cascade Reactions
  • 9.3.1 Catalytic Systems Combining Multiple Amine Catalysts
  • 9.3.2 Catalytic Systems Combining Amine Catalysts and Nucleophilic Carbenes
  • 9.3.3 Catalytic Systems Combining Amine and Hydrogen-Bonding Donor Catalysts
  • 9.3.4 Catalytic Systems Involving Other Organocatalysts
  • 9.4 Metal/Organic Binary Catalytic System-Promoted Cascade Reactions
  • 9.4.1 Catalytic Systems Combining Secondary Amine and Metal Catalysts
  • 9.4.2 Catalytic Systems Combining Brønsted Acid and Metal Catalysts.

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