Applications of Domino Transformations in Organic Synthesis, Volume 2

Name: Applications of Domino Transformations in Organic Synthesis, Volume 2
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Science of Synthesis Applications of Domino Transformations in Organic Synthesis 2
Title Page
Copyright
Preface
Science of Synthesis Reference Library
Volume Editor's Preface
Abstracts
Applications of Domino Transformations in Organic Synthesis 2
Table of Contents
2.1 Pericyclic Reactions
2.1.1 The Diels-Alder Cycloaddition Reaction in the Context of Domino Processes
2.1.1.1 Cascades Not Initiated by Diels-Alder Reaction
2.1.1.1.1 Cascades Generating a Diene
2.1.1.1.1.1 Ionic Generation of a Diene
2.1.1.1.1.1.1 Through Wessely Oxidation of Phenols
2.1.1.1.1.1.2 Through Ionic Cyclization
2.1.1.1.1.1.3 Through Deprotonation of an Alkene
2.1.1.1.1.1.4 Through Elimination Reactions
2.1.1.1.1.1.5 Through Allylation
2.1.1.1.1.2 Pericyclic Generation of a Diene
2.1.1.1.1.2.1 Through Electrocyclization
2.1.1.1.1.2.1.1 Through Benzocyclobutene Ring Opening
2.1.1.1.1.2.1.2 Through Electrocyclic Ring Closure
2.1.1.1.1.2.2 Through Cycloaddition or Retrocycloaddition
2.1.1.1.1.2.3 Through Sigmatropic Reactions
2.1.1.1.1.3 Photochemical Generation of a Diene
2.1.1.1.1.4 Metal-Mediated Generation of a Diene
2.1.1.1.2 Cascades Generating a Dienophile
2.1.1.1.2.1 Ionic Generation of a Dienophile
2.1.1.1.2.1.1 Through Himbert Cycloadditions
2.1.1.1.2.1.2 Through Benzyne Formation
2.1.1.1.2.1.3 Through Wessely Oxidation
2.1.1.1.2.2 Pericyclic Generation of a Dienophile
2.1.1.1.2.2.1 Through Cycloaddition/Retrocycloaddition
2.1.1.1.2.2.2 Through Sigmatropic Rearrangement
2.1.1.1.2.2.3 Through Electrocyclization
2.1.1.1.3 Proximity-Induced Diels-Alder Reactions
2.1.1.2 Diels-Alder as the Initiator of a Cascade
2.1.1.2.1 Pericyclic Reactions Occurring in the Wake of a Diels-Alder Reaction
2.1.1.2.1.1 Cascades Featuring Diels-Alder/Diels-Alder Processes
2.1.1.2.1.2 Cascades Featuring Diels-Alder/Retro-Diels-Alder Processes
2.1.1.2.1.3 [4 + 2] Cycloaddition with Subsequent Desaturation
2.1.1.2.2 Diels-Alder Reactions with Concomitant Ionic Structural Rearrangements
2.1.1.2.2.1 Pairings of Diels-Alder Reactions with Structural Fragmentations
2.1.1.2.2.2 Combining a Diels-Alder Reaction with Ionic Cyclization
2.1.1.3 Conclusions
2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions
2.1.2.1 Domino [2 + 2] Cycloadditions
2.1.2.1.1 Cycloaddition of an Enaminone and ß-Diketone with Fragmentation
2.1.2.1.2 Cycloaddition of Ynolate Anions Followed by Dieckmann Condensation/Michael Reaction
2.1.2.1.3 Cycloaddition Cascade Involving Benzyne-Enamide Cycloaddition or a Fischer Carbene Complex
2.1.2.1.4 Cycloadditions with Rearrangement
2.1.2.1.4.1 Cycloaddition of an Azatriene Followed by Cope Rearrangement
2.1.2.1.4.2 Cycloaddition of a Propargylic Ether and Propargylic Thioether Followed by [3,3]-Sigmatropic Rearrangement
2.1.2.1.4.3 [3,3]-Sigmatropic Rearrangement of Propargylic Ester and Propargylic Acetate Followed by Cycloaddition
2.1.2.1.4.4 Cycloaddition of a Ketene Followed by Allylic Rearrangement
2.1.2.1.4.5 Allyl Migration in Ynamides Followed by Cycloaddition
2.1.2.1.4.6 1,3-Migration in Propargyl Benzoates Followed by Cycloaddition
2.1.2.2 Domino [3 + 2] Cycloadditions
2.1.2.2.1 Cycloadditions with Nitrones, Nitronates, and Nitrile Oxides
2.1.2.2.1.1 Reaction To Give a Nitrone Followed by Cycloaddition
2.1.2.2.1.2 Cycloaddition with a Nitrone and Subsequent Reaction
2.1.2.2.1.3 Reaction To Give a Nitronate Followed by Cycloaddition
2.1.2.2.1.4 Reaction To Give a Nitrile Oxide Followed by Cycloaddition
2.1.2.2.1.5 Cycloaddition with a Nitrile Oxide and Subsequent Reaction
2.1.2.2.2 Cycloadditions with Carbonyl Ylides
2.1.2.2.2.1 Reaction of an a-Diazo Compound To Give a Carbonyl Ylide Followed by Cycloaddition
2.1.2.2.2.2 Reaction of an Alkyne To Give a Carbonyl Ylide Followed by Cycloaddition
2.1.2.2.3 Cycloadditions with Azomethine Ylides
2.1.2.2.4 Cycloadditions with Azomethine Imines
2.1.2.2.5 Cycloadditions with Azides
2.1.2.2.5.1 Reaction To Give an Azido-Substituted Alkyne Followed by Cycloaddition
2.1.2.2.5.2 Cycloaddition of an Azide and Subsequent Reaction
2.1.2.3 Domino [5 + 2] Cycloadditions
2.1.2.3.1 Cycloaddition of a Vinylic Oxirane Followed by Claisen Rearrangement
2.1.2.3.2 Cycloaddition of an Ynone Followed by Nazarov Cyclization
2.1.2.3.3 Cycloaddition of an Acetoxypyranone Followed by Conjugate Addition
2.1.2.3.4 Cycloaddition Cascade Involving ?-Pyranone and Quinone Systems
2.1.3 Domino Transformations Involving an Electrocyclization Reaction
2.1.3.1 Metal-Mediated Cross Coupling Followed by Electrocyclization
2.1.3.1.1 Palladium-Mediated Cross Coupling/Electrocyclization Reactions
2.1.3.1.1.1 Cross Coupling/6p-Electrocyclization
2.1.3.1.1.2 Cross Coupling/8p-Electrocyclization
2.1.3.1.1.3 Cross Coupling/8p-Electrocyclization/6p-Electrocyclization
2.1.3.1.2 Copper-Catalyzed Tandem Reactions
2.1.3.1.3 Zinc-Catalyzed Tandem Reactions
2.1.3.1.4 Ruthenium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reactions
2.1.3.2 Alkyne Transformation Followed by Electrocyclization
2.1.3.3 Isomerization Followed by Electrocyclization
2.1.3.3.1 1,3-Hydrogen Shift/Electrocyclization
2.1.3.3.2 1,5-Hydrogen Shift/Electrocyclization
2.1.3.3.3 1,7-Hydrogen Shift/Electrocyclization
2.1.3.4 Consecutive Electrocyclization Reaction Cascades
2.1.3.5 Alkenation Followed by Electrocyclization
2.1.3.6 Electrocyclization Followed by Cycloaddition
2.1.3.7 Miscellaneous Reactions
2.1.3.7.1 Electrocyclization/Oxidation
2.1.3.7.2 Photochemical Elimination/Electrocyclization
2.1.3.7.3 Domino Retro-electrocyclization Reactions
2.1.3.8 Hetero-electrocyclization
2.1.3.8.1 Aza-electrocyclization
2.1.3.8.1.1 Metal-Mediated Reaction/Hetero-electrocyclization
2.1.3.8.1.2 Imine or Iminium Formation/Hetero-electrocyclization
2.1.3.8.1.3 Isomerization or Rearrangement/Hetero-electrocyclization
2.1.3.8.2 Oxa-electrocyclization
2.1.3.8.3 Thia-electrocyclization
2.1.4 Sigmatropic Shifts and Ene Reactions (Excluding [3,3])
2.1.4.1 Practical Considerations
2.1.4.2 Domino Processes Initiated by Ene Reactions
2.1.4.3 Domino Processes Initiated by [2,3]-Sigmatropic Rearrangements
2.1.4.4 Domino Processes Initiated by Other Sigmatropic Rearrangements
2.1.4.5 Domino Processes in the Synthesis of Natural Products
2.1.4.6 Conclusions
2.1.5 Domino Transformations Initiated by or Proceeding Through [3,3]-Sigmatropic Rearrangements
2.1.5.1 Cope Rearrangement Followed by Enolate Functionalization
2.1.5.1.1 Anionic Oxy-Cope Rearrangement Followed by Intermolecular Enolate Alkylation with Alkyl Halides
2.1.5.1.2 Anionic Oxy-Cope Rearrangement Followed by Enolate Alkylation by Pendant Allylic Ethers
2.1.5.1.3 Anionic Oxy-Cope Rearrangement Followed by Enolate Acylation
2.1.5.2 Aza- and Oxonia-Cope-Containing Domino Sequences
2.1.5.2.1 Ionization-Triggered Oxonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by an Enol Silyl Ether
2.1.5.2.2 Intermolecular 1,4-Addition-Triggered Oxonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by a Nascent Enolate
2.1.5.2.3 Iminium-Ion-Formation-Triggered Azonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by a Nascent Enamine
2.1.5.3 Double, Tandem Hetero-Cope Rearrangement Processes
2.1.5.3.1 Double, Tandem [3,3]-Sigmatropic Rearrangement of Allylic, Homoallylic Bis (trichloroacetimidates)
2.1.5.4 Neutral Claisen Rearrangement Followed by Further (Non-Claisen) Processes
2.1.5.4.1 Oxy-Cope Rearrangement/Ene Reaction Domino Sequences
2.1.5.4.2 Oxy-Cope Rearrangement/Ene Reaction/Claisen Rearrangement and Oxy-Cope Rearrangement/Claisen Rearrangement/Ene Reaction Domino Sequences
2.1.5.5 Claisen Rearrangement Followed by Another Pericyclic Process
2.1.5.5.1 Double, Tandem Bellus-Claisen Rearrangement Reactions
2.1.5.5.2 Claisen Rearrangement Followed by [2,3]-Sigmatropic Rearrangement
2.1.5.5.3 Claisen Rearrangement/Diels-Alder Cycloaddition Domino Sequences
2.1.5.5.4 Claisen Rearrangement/[1,5]-H-Shift/6p-Electrocyclization Domino Sequences
2.1.5.6 Claisen Rearrangement Followed by Multiple Processes
2.1.5.6.1 Propargyl Claisen Rearrangement Followed by Tautomerization, Acylketene Generation, 6p-Electrocyclization, and Aromatization
2.1.5.6.2 Propargyl Claisen Rearrangement Followed by Imine Formation, Tautomerization, and 6p-Electrocyclization
2.2 Intermolecular Alkylative Dearomatizations of Phenolic Derivatives in Organic Synthesis
2.2.1 Metal-Mediated Intermolecular Alkylative Dearomatization
2.2.1.1 Osmium (II)-Mediated Intermolecular Alkylative Dearomatization
2.2.1.2 Palladium-Catalyzed Intermolecular Alkylative Dearomatization
2.2.1.3 Tandem Palladium-Catalyzed Intermolecular Alkylative Dearomatization/Annulation
2.2.2 Non-Metal-Mediated Intermolecular Alkylative Dearomatization
2.2.2.1 Alkylative Dearomatizations of Phenolic Derivatives with Activated Electrophiles
2.2.2.2 Alkylative Dearomatizations of Phenolic Derivatives with Unactivated Electrophiles
2.2.3 Tandem Intermolecular Alkylative Dearomatization/Annulation
2.2.3.1 Tandem Alkylative Dearomatization/[4 + 2] Cycloaddition
2.2.3.2 Tandem Alkylative Dearomatization/Hydrogenation Followed by Lewis Acid Catalyzed Cyclization
2.2.3.3 Tandem Alkylative Dearomatization/Annulation To Access Type A and B Polyprenylated Acylphloroglucinol Derivatives
2.2.3.4 Enantioselective, Tandem Alkylative Dearomatization/Annulation
2.2.3.5 Tandem Alkylative Dearomatization/Radical Cyclization
2.2.4 Recent Methods for Alkylative Dearomatization of Phenolic Derivatives
2.2.4.1 Recent Applications to Intermolecular Alkylative Dearomatization of Naphthols
2.2.4.2 Dearomatization Reactions as Domino Transformations To Access Type A and B Polyprenylated Acylphloroglucinol Analogues
2.3 Additions to Alkenes and C=O and C=N Bonds
2.3.1 Additions to Nonactivated C=C Bonds
2.3.1.1 Domino Amination
2.3.1.1.1 Proton-Initiated Events
2.3.1.1.2 Transition-Metal-Initiated Events
2.3.1.1.3 Halogen-Initiated Events
2.3.1.2 Domino Etherification
2.3.1.2.1 Halogen-Initiated Events
2.3.1.3 Domino Carbonylation
2.3.1.3.1 Transition-Metal-Initiated Events
2.3.1.3.2 Halogen-Initiated Events
2.3.1.4 Domino Polyene Cyclization
2.3.1.4.1 Transition-Metal-Initiated Events
2.3.1.4.2 Halogen-Initiated Events
2.3.1.4.3 Chalcogen-Initiated Events
2.3.2 Organocatalyzed Addition to Activated C=C Bonds
2.3.2.1 Organocatalyzed Domino Reactions with Activated Alkenes: The First Examples
2.3.2.1.1 Prolinol Trimethylsilyl Ethers as Privileged Catalysts for Enamine and Iminium Ion Activation
2.3.2.1.2 Increasing Complexity in Organocatalyzed Domino Reactions
2.3.2.2 Domino Organocatalyzed Reactions of Oxindole Derivatives
2.3.2.2.1 From Enders' Domino Reactions to Melchiorre's Methylene Oxindole
2.3.2.2.2 Michael Addition to Oxindoles
2.3.2.3 Synthesis of Tamiflu: The Hayashi Approach
2.3.2.4 One-Pot Synthesis of ABT-341, a DPP4-Selective Inhibitor
2.3.2.5 Large-Scale Industrial Application of Organocatalytic Domino Reactions: A Case Study
2.3.2.5.1 Transferring Organocatalytic Reactions from Academia to Industry: Not Straightforward
2.3.2.5.2 The Reaction Developed in the Academic Environment
2.3.2.5.3 The Reaction Developed in the Industrial Environment
2.3.3 Addition to Monofunctional C=O Bonds
2.3.3.1 Transition-Metal-Catalyzed Domino Addition to C=O Bonds
2.3.3.1.1 Domino Reactions Involving Carbonyl Ylides
2.3.3.1.2 Reductive Aldol Reactions
2.3.3.1.3 Michael/Aldol Reactions
2.3.3.1.4 Other Domino Addition Reactions
2.3.3.2 Organocatalytic Domino Addition to C=O Bonds
2.3.3.2.1 Amine-Catalyzed Domino Addition to C=O Bonds
2.3.3.2.1.1 Enamine-Catalyzed Aldol/Aldol Reactions
2.3.3.2.1.2 Enamine-Catalyzed Aldol/Michael Reactions
2.3.3.2.1.3 Enamine-Catalyzed Diels-Alder Reactions
2.3.3.2.1.4 Enamine-Catalyzed Michael/Henry Reactions
2.3.3.2.1.5 Enamine-Catalyzed Michael/Aldol Reactions
2.3.3.2.1.6 Enamine-Catalyzed Michael/Hemiacetalization Reactions
2.3.3.2.1.7 Iminium-Catalyzed Michael/Aldol Reactions
2.3.3.2.1.8 Iminium-Catalyzed Michael/Henry Reactions
2.3.3.2.1.9 Iminium-Catalyzed Michael/Morita-Baylis-Hillman Reactions
2.3.3.2.1.10 Iminium-Catalyzed Michael/Hemiacetalization Reactions
2.3.3.2.2 Thiourea-Catalyzed Domino Addition to C=O Bonds
2.3.3.2.2.1 Aldol/Cyclization Reactions
2.3.3.2.2.2 Michael/Aldol Reactions
2.3.3.2.2.3 Michael/Henry Reactions
2.3.3.2.2.4 Michael/Hemiacetalization Reactions
2.3.3.2.3 Phosphoric Acid Catalyzed Domino Addition to C=O Bonds
2.3.3.3 Lewis Acid Catalyzed Domino Addition to C=O Bonds
2.3.3.4 Conclusions
2.3.4 Additions to C=N Bonds and Nitriles
2.3.4.1 Addition to C=N Bonds and the Pictet-Spengler Strategy
2.3.4.2 Ugi Five-Center Four-Component Reaction Followed by Postcondensations
2.3.4.3 Addition to Nitriles
Keyword Index
Author Index
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Applications of Domino Transformations in Organic Synthesis, Volume 2

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