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Methods and Applications of Cycloaddition Reactions in Organic Syntheses.
Organic Syntheses enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Hoboken :
Wiley,
2013.
|
| Temas: | |
| Acceso en línea: | Texto completo |
Tabla de Contenidos:
- Methods and Applications of Cycloaddition Reactions in Organic Syntheses
- Contents
- Preface
- Contributors
- Part I: [2+1] Cycloaddition
- 1 [2+1]-Type Cyclopropanation Reactions
- 1.1 INTRODUCTION
- 1.2 CYCLOPROPANATION REACTION VIA MICHAEL-INDUCED RING CLOSURE REACTION
- 1.2.1 Introduction
- 1.2.2 Halo-Substituted Nucleophiles in MIRC Reaction
- 1.2.3 Ylides for Cyclopropanation
- 1.3 SIMMONS-SMITH CYCLOPROPANATION AND RELATED REACTIONS
- 1.3.1 Introduction
- 1.3.2 The Simmons-Smith Reaction with Zinc Reagents
- 1.4 DIAZOALKANES WITH TRANSITION METAL CATALYSTS
- 1.4.1 Introduction
- 1.4.2 Rhodium-Catalyzed Reactions
- 1.4.4 Ruthenium-Catalyzed Reactions
- 1.4.5 Cobalt- and Iron-Catalyzed Reactions
- 1.4.6 Other Transition Metal-Catalyzed Reactions
- 1.4.7 Cyclopropanation Without Transition Metal Catalysts
- 1.4.8 Cyclopropanation of Dihalocarbenes
- 1.5 CYCLOISOMERIZATION WITH TRANSITION METAL CATALYSTS
- 1.5.1 Introduction
- 1.5.2 Gold Complex-Catalyzed Reactions
- 1.5.3 Palladium Complex-Catalyzed Reactions
- 1.5.4 Platinum Complex-Catalyzed Reactions
- 1.5.5 Ruthenium Complex-Catalyzed Reactions
- 1.5.6 Other Metal Complex-Catalyzed Reactions
- 1.6 KULINKOVICH REACTIONS
- 1.6.1 Introduction
- 1.6.2 The Kulinkovich Reaction to Esters, Ketones, and Amides
- 1.6.3 Kulinkovich Reaction to Nitriles
- 1.6.4 Other Ti-Mediated Cyclopropanation Reactions
- 1.7 MISCELLANEOUS [2+1]-TYPE OF CYCLOPROPANATION REACTIONS
- REFERENCES
- 2 N1 Unit Transfer Reaction To C-C Double Bonds
- 2.1 INTRODUCTION
- 2.2 AZIRIDINATION WITH AZIDES
- 2.3 AZIRIDINATION WITH IMINOIODINANES
- 2.4 AZIRIDINATION WITH N-HALOAMINE SALTS
- 2.5 AZIRIDINATION WITH OTHER N1 UNIT
- 2.6 CONCLUSIONS
- REFERENCES
- Part II: [2+2] Cycloaddition
- 3 Lewis Base Catalyzed Asymmetric Formal [2+2] Cycloadditions
- 3.1 INTRODUCTION.
- 6.4 CHIRAL AND (E)-GEOMETRY-FIXED NITRONE
- 6.4.1 Design, Synthesis, and Cycloaddition of Cyclic Alkoxycarbonylnitrones
- 6.4.2 Chelation Controlled Cycloaddition of Cyclic Alkoxycarbonylnitrone with Allyl Alcohols
- 6.4.3 Syntheses of 4-Hydroxy-4-Substituted Glutamic Acid Using Cycloaddition of (S)-Cyclic Alkoxycarbonylnitrone
- 6.4.4 Synthesis of Maremycins Via Cycloaddition of (S)-Cyclic Alkoxycarbonylnitrone
- 6.5 CONCLUSIONS
- REFERENCES
- 7 Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Imines, Nitrile Oxides, Diazoalkanes, and Carbonyl Ylides
- 7.1 INTRODUCTION
- 7.2 ASYMMETRIC CYCLOADDITION OF AZOMETHINE IMINE
- 7.2.1 Copper-Catalyzed [3+2] Reaction of Terminal Alkyne
- 7.2.2 Chiral Lewis Acid-Catalyzed Cycloaddition
- 7.2.3 Organocatalytic 1,3-Dipolar Cycloaddition
- 7.2.4 1,3-Dipolar Cycloaddition with Allylic Alcohol and Homoallylic Alcohol
- 7.3 ASYMMETRIC CYCLOADDITION OF DIAZOALKANE
- 7.3.1 Cycloaddition of Trimethylsilyldiazomethane
- 7.3.2 Cycloaddition of Diazoacetate
- 7.4 ASYMMETRIC CYCLOADDITION OF NITRILE OXIDE
- 7.4.1 1,3-Dipolar Cycloaddition with Allylic Alcohol
- 7.4.2 Chiral Lewis Acid-Catalyzed Cycloaddition
- 7.5 ASYMMETRIC CYCLOADDITION OF CARBONYL YLIDE
- 7.5.1 Chiral Rh-Catalyzed Cycloaddition- Monoactivation
- 7.5.2 Chiral Lewis Acid-Catalyzed Cycloaddition- Dual Activation
- 7.6 CONCLUSIONS
- REFERENCES
- 8 Condensation of Primary Nitro Compounds to Isoxazole Derivatives: Stoichiometric to Catalytic
- 8.1 INTRODUCTION
- 8.2 CATALYTIC CONDENSATION OF "ACTIVE" NITRO COMPOUNDS
- 8.2.1 The Choice of Solvent
- 8.2.2 Induction Time
- 8.2.3 Acid-Base Catalysis
- 8.2.4 Selectivity, Competition with Other Reactions
- 8.2.5 Furoxans
- 8.3 COPPER CATALYSIS AND CONDENSATION OF NITROALKANES
- 8.4 MECHANISM FOR ACTIVATED NITRO COMPOUNDS
- 8.4.1 Mechanism in Water.
- 8.4.2 Mechanism in Chloroform
- 8.4.3 Mechanism in the Presence of Copper
- 8.5 SYNTHETIC APPLICATIONS AND TABULAR SURVEY
- 8.5.1 Condensation with Base Catalysis in Chloroform
- 8.5.2 Condensation with Base and CuII Catalysis in Chloroform
- 8.5.3 Condensation with Base Catalysis in Ethanol
- 8.5.4 Condensation with Base Catalysis in Water
- ACKNOWLEDGMENTS
- REFERENCES
- 9 Carbamoylnitrile Oxide and Inverse Electron-Demand 1,3-Dipolar Cycloaddition
- 9.1 INTRODUCTION
- 9.2 DIVERSE REACTIVITY OF NITROISOXAZOLONE DERIVATIVES
- 9.3 CYCLOADDITION OF CARBAMOYLNITRILE OXIDE IN AQUEOUS MEDIA
- 9.4 MECHANISTIC STUDY ON GENERATION OF NITRILE OXIDE
- 9.5 ISOLATION OF 1,2,4-OXADIAZOLE DERIVATIVE
- 9.6 OPTIMIZATION OF REACTION CONDITIONS FOR PREPARATION OF 5-METHYLOXADIAZOLE
- 9.7 SYNTHESES OF OTHER 3-CARBAMOYL-1,2,4- OXADIAZOLES
- 9.8 ACTIVATION OF A NITRILE BY A CARBAMOYL GROUP
- 9.9 CYCLOADDITION OF NITRILE OXIDE WITH 1,3-DICARBONYL COMPOUNDS
- 9.10 ACTIVATION OF KETO ESTER BY COORDINATION WITH METAL IONS
- 9.11 CYCLOADDITION WITH OTHER 1,3-DICARBONYL COMPOUNDS
- 9.12 SUMMARY
- REFERENCES
- Part V: [3+2], [3+3], and [4+2] Cycloaddition
- 10 Cycloaddition Reactions of Small Rings
- 10.1 INTRODUCTION
- 10.2 USE OF ORGANOMETALLIC COMPLEXES IN THE [3+2] CYCLOADDITION REACTION WITH CYCLOPROPANES
- 10.3 USE OF DICOBALT COMPLEXES IN THE [4+2] CYCLOADDITION REACTION WITH CYCLOBUTANES
- 10.4 OTHER DIPOLAR CYCLOADDITION REACTIONS
- 10.5 USE OF [3+3] DIPOLAR CYCLOADDITIONS IN THE SYNTHESIS OF OXAZINE DERIVATIVES
- 10.6 INTRAMOLECULAR [3+2] CYCLOADDITION REACTIONS
- 10.7 SYNTHESIS OF TETRAHYDROFURAN DERIVATIVES VIA THE [3+2] CYCLOADDITION REACTION
- 10.8 APPLICATIONS OF [3+2] CYCLOADDITION REACTION TO NATURAL PRODUCTS
- 10.9 SYNTHESIS OF PYRROLIDINES AND PYRAZOLINES DERIVATIVES VIA THE CYCLOADDITION REACTION.