Applications of Domino Transformations in Organic Synthesis, Volume 2

Name: Applications of Domino Transformations in Organic Synthesis, Volume 2
Brand: Thieme
Price: 259.99 EUR
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Scott A. Snyder(Herausgeber*in)

Thieme (Verlag)

1. Auflage

Erschienen am 11. Mai 2016

528 Seiten

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1 - Science of Synthesis Applications of Domino Transformations in Organic Synthesis 2 [Seite 1]
2 - Title Page [Seite 7]
3 - Copyright [Seite 8]
4 - Preface [Seite 9]
5 - Science of Synthesis Reference Library [Seite 11]
6 - Volume Editor's Preface [Seite 13]
7 - Abstracts [Seite 15]
8 - Applications of Domino Transformations in Organic Synthesis 2 [Seite 21]
9 - Table of Contents [Seite 23]
10 - 2.1 Pericyclic Reactions [Seite 31]
10.1 - 2.1.1 The Diels-Alder Cycloaddition Reaction in the Context of Domino Processes [Seite 31]
10.1.1 - 2.1.1.1 Cascades Not Initiated by Diels-Alder Reaction [Seite 32]
10.1.1.1 - 2.1.1.1.1 Cascades Generating a Diene [Seite 32]
10.1.1.1.1 - 2.1.1.1.1.1 Ionic Generation of a Diene [Seite 32]
10.1.1.1.1.1 - 2.1.1.1.1.1.1 Through Wessely Oxidation of Phenols [Seite 32]
10.1.1.1.1.2 - 2.1.1.1.1.1.2 Through Ionic Cyclization [Seite 36]
10.1.1.1.1.3 - 2.1.1.1.1.1.3 Through Deprotonation of an Alkene [Seite 37]
10.1.1.1.1.4 - 2.1.1.1.1.1.4 Through Elimination Reactions [Seite 38]
10.1.1.1.1.5 - 2.1.1.1.1.1.5 Through Allylation [Seite 42]
10.1.1.1.2 - 2.1.1.1.1.2 Pericyclic Generation of a Diene [Seite 42]
10.1.1.1.2.1 - 2.1.1.1.1.2.1 Through Electrocyclization [Seite 43]
10.1.1.1.2.1.1 - 2.1.1.1.1.2.1.1 Through Benzocyclobutene Ring Opening [Seite 43]
10.1.1.1.2.1.2 - 2.1.1.1.1.2.1.2 Through Electrocyclic Ring Closure [Seite 44]
10.1.1.1.2.2 - 2.1.1.1.1.2.2 Through Cycloaddition or Retrocycloaddition [Seite 47]
10.1.1.1.2.3 - 2.1.1.1.1.2.3 Through Sigmatropic Reactions [Seite 48]
10.1.1.1.3 - 2.1.1.1.1.3 Photochemical Generation of a Diene [Seite 49]
10.1.1.1.4 - 2.1.1.1.1.4 Metal-Mediated Generation of a Diene [Seite 50]
10.1.1.2 - 2.1.1.1.2 Cascades Generating a Dienophile [Seite 52]
10.1.1.2.1 - 2.1.1.1.2.1 Ionic Generation of a Dienophile [Seite 52]
10.1.1.2.1.1 - 2.1.1.1.2.1.1 Through Himbert Cycloadditions [Seite 52]
10.1.1.2.1.2 - 2.1.1.1.2.1.2 Through Benzyne Formation [Seite 53]
10.1.1.2.1.3 - 2.1.1.1.2.1.3 Through Wessely Oxidation [Seite 54]
10.1.1.2.2 - 2.1.1.1.2.2 Pericyclic Generation of a Dienophile [Seite 57]
10.1.1.2.2.1 - 2.1.1.1.2.2.1 Through Cycloaddition/Retrocycloaddition [Seite 57]
10.1.1.2.2.2 - 2.1.1.1.2.2.2 Through Sigmatropic Rearrangement [Seite 57]
10.1.1.2.2.3 - 2.1.1.1.2.2.3 Through Electrocyclization [Seite 59]
10.1.1.3 - 2.1.1.1.3 Proximity-Induced Diels-Alder Reactions [Seite 59]
10.1.2 - 2.1.1.2 Diels-Alder as the Initiator of a Cascade [Seite 61]
10.1.2.1 - 2.1.1.2.1 Pericyclic Reactions Occurring in the Wake of a Diels-Alder Reaction [Seite 61]
10.1.2.1.1 - 2.1.1.2.1.1 Cascades Featuring Diels-Alder/Diels-Alder Processes [Seite 61]
10.1.2.1.2 - 2.1.1.2.1.2 Cascades Featuring Diels-Alder/Retro-Diels-Alder Processes [Seite 63]
10.1.2.1.3 - 2.1.1.2.1.3 [4 + 2] Cycloaddition with Subsequent Desaturation [Seite 66]
10.1.2.2 - 2.1.1.2.2 Diels-Alder Reactions with Concomitant Ionic Structural Rearrangements [Seite 66]
10.1.2.2.1 - 2.1.1.2.2.1 Pairings of Diels-Alder Reactions with Structural Fragmentations [Seite 67]
10.1.2.2.2 - 2.1.1.2.2.2 Combining a Diels-Alder Reaction with Ionic Cyclization [Seite 70]
10.1.3 - 2.1.1.3 Conclusions [Seite 73]
10.2 - 2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions [Seite 77]
10.2.1 - 2.1.2.1 Domino [2 + 2] Cycloadditions [Seite 77]
10.2.1.1 - 2.1.2.1.1 Cycloaddition of an Enaminone and ß-Diketone with Fragmentation [Seite 78]
10.2.1.2 - 2.1.2.1.2 Cycloaddition of Ynolate Anions Followed by Dieckmann Condensation/Michael Reaction [Seite 78]
10.2.1.3 - 2.1.2.1.3 Cycloaddition Cascade Involving Benzyne-Enamide Cycloaddition or a Fischer Carbene Complex [Seite 80]
10.2.1.4 - 2.1.2.1.4 Cycloadditions with Rearrangement [Seite 81]
10.2.1.4.1 - 2.1.2.1.4.1 Cycloaddition of an Azatriene Followed by Cope Rearrangement [Seite 81]
10.2.1.4.2 - 2.1.2.1.4.2 Cycloaddition of a Propargylic Ether and Propargylic Thioether Followed by [3,3]-Sigmatropic Rearrangement [Seite 82]
10.2.1.4.3 - 2.1.2.1.4.3 [3,3]-Sigmatropic Rearrangement of Propargylic Ester and Propargylic Acetate Followed by Cycloaddition [Seite 83]
10.2.1.4.4 - 2.1.2.1.4.4 Cycloaddition of a Ketene Followed by Allylic Rearrangement [Seite 84]
10.2.1.4.5 - 2.1.2.1.4.5 Allyl Migration in Ynamides Followed by Cycloaddition [Seite 85]
10.2.1.4.6 - 2.1.2.1.4.6 1,3-Migration in Propargyl Benzoates Followed by Cycloaddition [Seite 86]
10.2.2 - 2.1.2.2 Domino [3 + 2] Cycloadditions [Seite 87]
10.2.2.1 - 2.1.2.2.1 Cycloadditions with Nitrones, Nitronates, and Nitrile Oxides [Seite 87]
10.2.2.1.1 - 2.1.2.2.1.1 Reaction To Give a Nitrone Followed by Cycloaddition [Seite 88]
10.2.2.1.2 - 2.1.2.2.1.2 Cycloaddition with a Nitrone and Subsequent Reaction [Seite 92]
10.2.2.1.3 - 2.1.2.2.1.3 Reaction To Give a Nitronate Followed by Cycloaddition [Seite 93]
10.2.2.1.4 - 2.1.2.2.1.4 Reaction To Give a Nitrile Oxide Followed by Cycloaddition [Seite 94]
10.2.2.1.5 - 2.1.2.2.1.5 Cycloaddition with a Nitrile Oxide and Subsequent Reaction [Seite 95]
10.2.2.2 - 2.1.2.2.2 Cycloadditions with Carbonyl Ylides [Seite 96]
10.2.2.2.1 - 2.1.2.2.2.1 Reaction of an a-Diazo Compound To Give a Carbonyl Ylide Followed by Cycloaddition [Seite 96]
10.2.2.2.2 - 2.1.2.2.2.2 Reaction of an Alkyne To Give a Carbonyl Ylide Followed by Cycloaddition [Seite 102]
10.2.2.3 - 2.1.2.2.3 Cycloadditions with Azomethine Ylides [Seite 103]
10.2.2.4 - 2.1.2.2.4 Cycloadditions with Azomethine Imines [Seite 110]
10.2.2.5 - 2.1.2.2.5 Cycloadditions with Azides [Seite 111]
10.2.2.5.1 - 2.1.2.2.5.1 Reaction To Give an Azido-Substituted Alkyne Followed by Cycloaddition [Seite 111]
10.2.2.5.2 - 2.1.2.2.5.2 Cycloaddition of an Azide and Subsequent Reaction [Seite 113]
10.2.3 - 2.1.2.3 Domino [5 + 2] Cycloadditions [Seite 114]
10.2.3.1 - 2.1.2.3.1 Cycloaddition of a Vinylic Oxirane Followed by Claisen Rearrangement [Seite 115]
10.2.3.2 - 2.1.2.3.2 Cycloaddition of an Ynone Followed by Nazarov Cyclization [Seite 116]
10.2.3.3 - 2.1.2.3.3 Cycloaddition of an Acetoxypyranone Followed by Conjugate Addition [Seite 116]
10.2.3.4 - 2.1.2.3.4 Cycloaddition Cascade Involving .-Pyranone and Quinone Systems [Seite 117]
10.3 - 2.1.3 Domino Transformations Involving an Electrocyclization Reaction [Seite 123]
10.3.1 - 2.1.3.1 Metal-Mediated Cross Coupling Followed by Electrocyclization [Seite 123]
10.3.1.1 - 2.1.3.1.1 Palladium-Mediated Cross Coupling/Electrocyclization Reactions [Seite 123]
10.3.1.1.1 - 2.1.3.1.1.1 Cross Coupling/6p-Electrocyclization [Seite 123]
10.3.1.1.2 - 2.1.3.1.1.2 Cross Coupling/8p-Electrocyclization [Seite 131]
10.3.1.1.3 - 2.1.3.1.1.3 Cross Coupling/8p-Electrocyclization/6p-Electrocyclization [Seite 133]
10.3.1.2 - 2.1.3.1.2 Copper-Catalyzed Tandem Reactions [Seite 139]
10.3.1.3 - 2.1.3.1.3 Zinc-Catalyzed Tandem Reactions [Seite 139]
10.3.1.4 - 2.1.3.1.4 Ruthenium-Catalyzed Formal [2 + 2 + 2] Cycloaddition Reactions [Seite 140]
10.3.2 - 2.1.3.2 Alkyne Transformation Followed by Electrocyclization [Seite 141]
10.3.3 - 2.1.3.3 Isomerization Followed by Electrocyclization [Seite 146]
10.3.3.1 - 2.1.3.3.1 1,3-Hydrogen Shift/Electrocyclization [Seite 146]
10.3.3.2 - 2.1.3.3.2 1,5-Hydrogen Shift/Electrocyclization [Seite 147]
10.3.3.3 - 2.1.3.3.3 1,7-Hydrogen Shift/Electrocyclization [Seite 150]
10.3.4 - 2.1.3.4 Consecutive Electrocyclization Reaction Cascades [Seite 151]
10.3.5 - 2.1.3.5 Alkenation Followed by Electrocyclization [Seite 153]
10.3.6 - 2.1.3.6 Electrocyclization Followed by Cycloaddition [Seite 156]
10.3.7 - 2.1.3.7 Miscellaneous Reactions [Seite 157]
10.3.7.1 - 2.1.3.7.1 Electrocyclization/Oxidation [Seite 157]
10.3.7.2 - 2.1.3.7.2 Photochemical Elimination/Electrocyclization [Seite 158]
10.3.7.3 - 2.1.3.7.3 Domino Retro-electrocyclization Reactions [Seite 160]
10.3.8 - 2.1.3.8 Hetero-electrocyclization [Seite 160]
10.3.8.1 - 2.1.3.8.1 Aza-electrocyclization [Seite 160]
10.3.8.1.1 - 2.1.3.8.1.1 Metal-Mediated Reaction/Hetero-electrocyclization [Seite 161]
10.3.8.1.2 - 2.1.3.8.1.2 Imine or Iminium Formation/Hetero-electrocyclization [Seite 169]
10.3.8.1.3 - 2.1.3.8.1.3 Isomerization or Rearrangement/Hetero-electrocyclization [Seite 174]
10.3.8.2 - 2.1.3.8.2 Oxa-electrocyclization [Seite 180]
10.3.8.3 - 2.1.3.8.3 Thia-electrocyclization [Seite 184]
10.4 - 2.1.4 Sigmatropic Shifts and Ene Reactions (Excluding [3,3]) [Seite 189]
10.4.1 - 2.1.4.1 Practical Considerations [Seite 189]
10.4.2 - 2.1.4.2 Domino Processes Initiated by Ene Reactions [Seite 190]
10.4.3 - 2.1.4.3 Domino Processes Initiated by [2,3]-Sigmatropic Rearrangements [Seite 198]
10.4.4 - 2.1.4.4 Domino Processes Initiated by Other Sigmatropic Rearrangements [Seite 208]
10.4.5 - 2.1.4.5 Domino Processes in the Synthesis of Natural Products [Seite 213]
10.4.6 - 2.1.4.6 Conclusions [Seite 221]
10.5 - 2.1.5 Domino Transformations Initiated by or Proceeding Through [3,3]-Sigmatropic Rearrangements [Seite 225]
10.5.1 - 2.1.5.1 Cope Rearrangement Followed by Enolate Functionalization [Seite 226]
10.5.1.1 - 2.1.5.1.1 Anionic Oxy-Cope Rearrangement Followed by Intermolecular Enolate Alkylation with Alkyl Halides [Seite 226]
10.5.1.2 - 2.1.5.1.2 Anionic Oxy-Cope Rearrangement Followed by Enolate Alkylation by Pendant Allylic Ethers [Seite 228]
10.5.1.3 - 2.1.5.1.3 Anionic Oxy-Cope Rearrangement Followed by Enolate Acylation [Seite 229]
10.5.2 - 2.1.5.2 Aza- and Oxonia-Cope-Containing Domino Sequences [Seite 231]
10.5.2.1 - 2.1.5.2.1 Ionization-Triggered Oxonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by an Enol Silyl Ether [Seite 231]
10.5.2.2 - 2.1.5.2.2 Intermolecular 1,4-Addition-Triggered Oxonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by a Nascent Enolate [Seite 233]
10.5.2.3 - 2.1.5.2.3 Iminium-Ion-Formation-Triggered Azonia-Cope Rearrangement Followed by Intramolecular Nucleophilic Trapping by a Nascent Enamine [Seite 234]
10.5.3 - 2.1.5.3 Double, Tandem Hetero-Cope Rearrangement Processes [Seite 237]
10.5.3.1 - 2.1.5.3.1 Double, Tandem [3,3]-Sigmatropic Rearrangement of Allylic, Homoallylic Bis (trichloroacetimidates) [Seite 237]
10.5.4 - 2.1.5.4 Neutral Claisen Rearrangement Followed by Further (Non-Claisen) Processes [Seite 239]
10.5.4.1 - 2.1.5.4.1 Oxy-Cope Rearrangement/Ene Reaction Domino Sequences [Seite 239]
10.5.4.2 - 2.1.5.4.2 Oxy-Cope Rearrangement/Ene Reaction/Claisen Rearrangement and Oxy-Cope Rearrangement/Claisen Rearrangement/Ene Reaction Domino Sequences [Seite 241]
10.5.5 - 2.1.5.5 Claisen Rearrangement Followed by Another Pericyclic Process [Seite 243]
10.5.5.1 - 2.1.5.5.1 Double, Tandem Bellus-Claisen Rearrangement Reactions [Seite 243]
10.5.5.2 - 2.1.5.5.2 Claisen Rearrangement Followed by [2,3]-Sigmatropic Rearrangement [Seite 245]
10.5.5.3 - 2.1.5.5.3 Claisen Rearrangement/Diels-Alder Cycloaddition Domino Sequences [Seite 247]
10.5.5.4 - 2.1.5.5.4 Claisen Rearrangement/[1,5]-H-Shift/6p-Electrocyclization Domino Sequences [Seite 250]
10.5.6 - 2.1.5.6 Claisen Rearrangement Followed by Multiple Processes [Seite 252]
10.5.6.1 - 2.1.5.6.1 Propargyl Claisen Rearrangement Followed by Tautomerization, Acylketene Generation, 6p-Electrocyclization, and Aromatization [Seite 252]
10.5.6.2 - 2.1.5.6.2 Propargyl Claisen Rearrangement Followed by Imine Formation, Tautomerization, and 6p-Electrocyclization [Seite 253]
11 - 2.2 Intermolecular Alkylative Dearomatizations of Phenolic Derivatives in Organic Synthesis [Seite 259]
11.1 - 2.2.1 Metal-Mediated Intermolecular Alkylative Dearomatization [Seite 262]
11.1.1 - 2.2.1.1 Osmium (II)-Mediated Intermolecular Alkylative Dearomatization [Seite 262]
11.1.2 - 2.2.1.2 Palladium-Catalyzed Intermolecular Alkylative Dearomatization [Seite 266]
11.1.3 - 2.2.1.3 Tandem Palladium-Catalyzed Intermolecular Alkylative Dearomatization/Annulation [Seite 267]
11.2 - 2.2.2 Non-Metal-Mediated Intermolecular Alkylative Dearomatization [Seite 270]
11.2.1 - 2.2.2.1 Alkylative Dearomatizations of Phenolic Derivatives with Activated Electrophiles [Seite 270]
11.2.2 - 2.2.2.2 Alkylative Dearomatizations of Phenolic Derivatives with Unactivated Electrophiles [Seite 278]
11.3 - 2.2.3 Tandem Intermolecular Alkylative Dearomatization/Annulation [Seite 282]
11.3.1 - 2.2.3.1 Tandem Alkylative Dearomatization/[4 + 2] Cycloaddition [Seite 282]
11.3.2 - 2.2.3.2 Tandem Alkylative Dearomatization/Hydrogenation Followed by Lewis Acid Catalyzed Cyclization [Seite 282]
11.3.3 - 2.2.3.3 Tandem Alkylative Dearomatization/Annulation To Access Type A and B Polyprenylated Acylphloroglucinol Derivatives [Seite 284]
11.3.4 - 2.2.3.4 Enantioselective, Tandem Alkylative Dearomatization/Annulation [Seite 290]
11.3.5 - 2.2.3.5 Tandem Alkylative Dearomatization/Radical Cyclization [Seite 293]
11.4 - 2.2.4 Recent Methods for Alkylative Dearomatization of Phenolic Derivatives [Seite 298]
11.4.1 - 2.2.4.1 Recent Applications to Intermolecular Alkylative Dearomatization of Naphthols [Seite 298]
11.4.2 - 2.2.4.2 Dearomatization Reactions as Domino Transformations To Access Type A and B Polyprenylated Acylphloroglucinol Analogues [Seite 311]
12 - 2.3 Additions to Alkenes and C=O and C=N Bonds [Seite 323]
12.1 - 2.3.1 Additions to Nonactivated C=C Bonds [Seite 323]
12.1.1 - 2.3.1.1 Domino Amination [Seite 324]
12.1.1.1 - 2.3.1.1.1 Proton-Initiated Events [Seite 324]
12.1.1.2 - 2.3.1.1.2 Transition-Metal-Initiated Events [Seite 325]
12.1.1.3 - 2.3.1.1.3 Halogen-Initiated Events [Seite 328]
12.1.2 - 2.3.1.2 Domino Etherification [Seite 335]
12.1.2.1 - 2.3.1.2.1 Halogen-Initiated Events [Seite 336]
12.1.3 - 2.3.1.3 Domino Carbonylation [Seite 347]
12.1.3.1 - 2.3.1.3.1 Transition-Metal-Initiated Events [Seite 347]
12.1.3.2 - 2.3.1.3.2 Halogen-Initiated Events [Seite 350]
12.1.4 - 2.3.1.4 Domino Polyene Cyclization [Seite 352]
12.1.4.1 - 2.3.1.4.1 Transition-Metal-Initiated Events [Seite 353]
12.1.4.2 - 2.3.1.4.2 Halogen-Initiated Events [Seite 355]
12.1.4.3 - 2.3.1.4.3 Chalcogen-Initiated Events [Seite 359]
12.2 - 2.3.2 Organocatalyzed Addition to Activated C=C Bonds [Seite 367]
12.2.1 - 2.3.2.1 Organocatalyzed Domino Reactions with Activated Alkenes: The First Examples [Seite 367]
12.2.1.1 - 2.3.2.1.1 Prolinol Trimethylsilyl Ethers as Privileged Catalysts for Enamine and Iminium Ion Activation [Seite 374]
12.2.1.2 - 2.3.2.1.2 Increasing Complexity in Organocatalyzed Domino Reactions [Seite 377]
12.2.2 - 2.3.2.2 Domino Organocatalyzed Reactions of Oxindole Derivatives [Seite 379]
12.2.2.1 - 2.3.2.2.1 From Enders' Domino Reactions to Melchiorre's Methylene Oxindole [Seite 380]
12.2.2.2 - 2.3.2.2.2 Michael Addition to Oxindoles [Seite 387]
12.2.3 - 2.3.2.3 Synthesis of Tamiflu: The Hayashi Approach [Seite 395]
12.2.4 - 2.3.2.4 One-Pot Synthesis of ABT-341, a DPP4-Selective Inhibitor [Seite 402]
12.2.5 - 2.3.2.5 Large-Scale Industrial Application of Organocatalytic Domino Reactions: A Case Study [Seite 406]
12.2.5.1 - 2.3.2.5.1 Transferring Organocatalytic Reactions from Academia to Industry: Not Straightforward [Seite 406]
12.2.5.2 - 2.3.2.5.2 The Reaction Developed in the Academic Environment [Seite 407]
12.2.5.3 - 2.3.2.5.3 The Reaction Developed in the Industrial Environment [Seite 409]
12.3 - 2.3.3 Addition to Monofunctional C=O Bonds [Seite 417]
12.3.1 - 2.3.3.1 Transition-Metal-Catalyzed Domino Addition to C=O Bonds [Seite 417]
12.3.1.1 - 2.3.3.1.1 Domino Reactions Involving Carbonyl Ylides [Seite 417]
12.3.1.2 - 2.3.3.1.2 Reductive Aldol Reactions [Seite 419]
12.3.1.3 - 2.3.3.1.3 Michael/Aldol Reactions [Seite 423]
12.3.1.4 - 2.3.3.1.4 Other Domino Addition Reactions [Seite 424]
12.3.2 - 2.3.3.2 Organocatalytic Domino Addition to C=O Bonds [Seite 425]
12.3.2.1 - 2.3.3.2.1 Amine-Catalyzed Domino Addition to C=O Bonds [Seite 425]
12.3.2.1.1 - 2.3.3.2.1.1 Enamine-Catalyzed Aldol/Aldol Reactions [Seite 425]
12.3.2.1.2 - 2.3.3.2.1.2 Enamine-Catalyzed Aldol/Michael Reactions [Seite 426]
12.3.2.1.3 - 2.3.3.2.1.3 Enamine-Catalyzed Diels-Alder Reactions [Seite 427]
12.3.2.1.4 - 2.3.3.2.1.4 Enamine-Catalyzed Michael/Henry Reactions [Seite 429]
12.3.2.1.5 - 2.3.3.2.1.5 Enamine-Catalyzed Michael/Aldol Reactions [Seite 430]
12.3.2.1.6 - 2.3.3.2.1.6 Enamine-Catalyzed Michael/Hemiacetalization Reactions [Seite 430]
12.3.2.1.7 - 2.3.3.2.1.7 Iminium-Catalyzed Michael/Aldol Reactions [Seite 432]
12.3.2.1.8 - 2.3.3.2.1.8 Iminium-Catalyzed Michael/Henry Reactions [Seite 434]
12.3.2.1.9 - 2.3.3.2.1.9 Iminium-Catalyzed Michael/Morita-Baylis-Hillman Reactions [Seite 434]
12.3.2.1.10 - 2.3.3.2.1.10 Iminium-Catalyzed Michael/Hemiacetalization Reactions [Seite 435]
12.3.2.2 - 2.3.3.2.2 Thiourea-Catalyzed Domino Addition to C=O Bonds [Seite 435]
12.3.2.2.1 - 2.3.3.2.2.1 Aldol/Cyclization Reactions [Seite 435]
12.3.2.2.2 - 2.3.3.2.2.2 Michael/Aldol Reactions [Seite 436]
12.3.2.2.3 - 2.3.3.2.2.3 Michael/Henry Reactions [Seite 437]
12.3.2.2.4 - 2.3.3.2.2.4 Michael/Hemiacetalization Reactions [Seite 438]
12.3.2.3 - 2.3.3.2.3 Phosphoric Acid Catalyzed Domino Addition to C=O Bonds [Seite 440]
12.3.3 - 2.3.3.3 Lewis Acid Catalyzed Domino Addition to C=O Bonds [Seite 441]
12.3.4 - 2.3.3.4 Conclusions [Seite 444]
12.4 - 2.3.4 Additions to C=N Bonds and Nitriles [Seite 449]
12.4.1 - 2.3.4.1 Addition to C=N Bonds and the Pictet-Spengler Strategy [Seite 452]
12.4.2 - 2.3.4.2 Ugi Five-Center Four-Component Reaction Followed by Postcondensations [Seite 458]
12.4.3 - 2.3.4.3 Addition to Nitriles [Seite 469]
13 - Keyword Index [Seite 479]
14 - Author Index [Seite 511]
15 - Abbreviations [Seite 527]

Abstracts

2.1.1 The Diels-Alder Cycloaddition Reaction in the Context of Domino Processes

J. G. West and E. J. Sorensen

The Diels-Alder cycloaddition has been a key component in innumerable, creative domino transformations in organic synthesis. This chapter provides examples of how this [4 + 2] cycloaddition has been incorporated into the said cascades, with particular attention to its interplay with the other reactions in the sequence. We hope that this review will assist the interested reader to approach the design of novel cascades involving the Diels-Alder reaction.

Keywords: Diels-Alder cascade domino reactions pericyclic [4 + 2] cycloaddition

2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions

I. Coldham and N. S. Sheikh

This chapter covers examples of domino reactions that include a [2 + 2]-, [3 + 2]-, or [5 + 2]-cycloaddition reaction. The focus is on concerted reactions that occur in a tandem sequence in one pot, rather than overall "formal cycloadditions" or multicomponent couplings. The cycloaddition step typically involves an alkene or alkyne as one of the components in the ring-forming reaction. In addition to the key cycloaddition step, another bond-forming reaction will be involved that can precede or follow the cycloaddition. This other reaction is often an alkylation that generates the substrate for the cycloaddition, or is a ring-opening or rearrangement reaction that occurs after the cycloaddition. As the chemistry involves sequential reactions including at least one ring-forming reaction, unusual molecular structures or compounds that can be difficult to prepare by other means can be obtained. As a result, this strategy has been used for the regio- and stereoselective preparation of a vast array of polycyclic, complex compounds of interest to diverse scientific communities.

Keywords: alkylation [2 + 2] cycloaddition [3 + 2] cycloaddition [5 + 2] cycloaddition dipolar cycloaddition domino reactions Nazarov cyclization ring formation [3,3]-sigmatropic rearrangement tandem reactions

2.1.3 Domino Transformations Involving an Electrocyclization Reaction

J. Suffert, M. Gulea, G. Blond, and M. Donnard

Electrocyclization processes represent a powerful and efficient way to produce carbo- or heterocycles stereoselectively. Moreover, when electrocyclizations are involved in domino processes, the overall transformation becomes highly atom and step economic, enabling access to structurally complex molecules. This chapter is devoted to significant contributions published in the last 15 years, focusing on synthetic methodologies using electrocyclization as a key step in a domino process.

Keywords: electrocyclization hetero-electrocyclization domino reactions cascade reactions

2.1.4 Sigmatropic Shifts and Ene Reactions (Excluding [3,3])

A. V. Novikov and A. Zakarian

This chapter features a review and discussion of the domino transformations initiated by ene reactions and sigmatropic rearrangements, particularly focusing on [2,3]-sigmatropic shifts, such as Mislow-Evans and Wittig rearrangements, and [1,n] hydrogen shifts. A variety of examples of these domino processes are reviewed, featuring such follow-up processes to the initial reaction as additional ene reactions or sigmatropic shifts, Diels-Alder cycloaddition, [3 + 2] cycloaddition, electrocyclization, condensation, and radical cyclization. General practical considerations and specific features in the examples of the reported cascade transformation are highlighted. To complete the discussion, uses of these cascade processes in the synthesis of natural products are discussed, demonstrating the rapid assembly of structural complexity that is characteristic of domino processes. Overall, the domino transformations initiated by ene reactions and sigmatropic shifts represent an important subset of domino processes, the study of which is highly valuable for understanding key aspects of chemical reactivity and development of efficient synthetic methods.

Keywords: ene reaction sigmatropic shift domino reactions cascade reactions hydrogen shift [1,3]-shift [1,5]-shift [1,7]-shift [2,3]-shift [3,3]-shift Mislow-Evans rearrangement Wittig rearrangement Diels-Alder cycloaddition Claisen rearrangement oxy-Cope rearrangement electrocyclization chloropupukeanolide D isocedrene steroids mesembrine joubertinamine pinnatoxins sterpurene arteannuin M pseudomonic acid A

2.1.5 Domino Transformations Initiated by or Proceeding Through [3,3]-Sigmatropic Rearrangements

C. A. Guerrero

This chapter concerns itself with domino transformations (i.e., cascade sequences and/or tandem reactions) that are either initiated by or proceed through at least one [3,3]-sigmatropic rearrangement. Excluded from this discussion are domino transformations that end with sigmatropy. The reactions included contain diverse forms of [3,3]-sigmatropic rearrangements and are followed by both polar chemistry or further concerted rearrangement.

Keywords: rearrangement sigmatropic Bellus-Claisen Cope Overman concerted stereoselective stereospecific ene trichloroacetimidate Diels-Alder

2.2 Intermolecular Alkylative Dearomatizations of Phenolic Derivatives in Organic Synthesis

J. A. Porco, Jr., and J. Boyce

Intermolecular alkylative dearomatization products have shown promise as synthetic intermediates with diverse capabilities. This chapter describes the available methods for constructing these dearomatized molecules and demonstrates their value as synthetic intermediates for efficient total syntheses.

Keywords: alkylative dearomatization dearomative alkylation dearomative substitution domino transformations domino sequences dearomative domino transformations cationic cyclization radical cyclization alkylative dearomatization/annulation

2.3.1 Additions to Nonactivated C=C Bonds

Z. W. Yu and Y.-Y. Yeung

Electrophilic additions to nonactivated C=C bonds are one of the well-known classical reactions utilized by synthetic chemists as a starting point to construct useful complex organic molecules. This chapter covers a collection of electrophile-initiated domino transformations involving alkenes as the first reaction, followed by reaction with suitable nucleophiles in the succession and termination reactions under identical conditions. The discussion focuses on recent advances in catalysis, strategically designed alkenes, and new electrophilic reagents employed to improve reactivity and control of stereochemistry in the sequence of bond-forming steps.

Keywords: nonactivated alkenes addition domino reactions amination etherification carbonylation polyenes protons halogens transition metals chalcogens

2.3.2 Organocatalyzed Addition to Activated C=C Bonds

P. Renzi, M. Moliterno, R. Salvio, and M. Bella

In this chapter, several examples of organocatalyzed additions to C=C bonds carried out through a domino approach are reviewed, from the early examples to recent applications of these strategies in industry.

Keywords: organocatalysis domino reactions iminium ions enamines Michael/aldol reactions nucleophilic/electrophilic addition a,ß-unsaturated carbonyl compounds spirocyclic oxindoles cinchona alkaloid derivatives chiral secondary amines Knoevenagel condensation methyleneindolinones

2.3.3 Addition to Monofunctional C=O Bonds

A. Song and W. Wang

Catalytic asymmetric domino addition to monofunctional C=O bonds is a powerful group of methods for the rapid construction of valuable chiral building blocks from readily available substances. Impressive progress has been made on transition-metal-catalyzed and organocatalytic systems that promote such addition processes through reductive aldol, Michael/aldol, or Michael/Henry sequences. In addition, Lewis acid catalysis has also been developed in this area for the synthesis of optically active chiral molecules. This chapter covers the most impressive examples of these recent developments in domino chemistry.

Keywords: aldol reactions carbonyl ylides chiral amine catalysis domino reactions epoxy alcohols Lewis acid catalysis Michael addition organocatalysis phosphoric acid catalysis thiourea catalysis

2.3.4 Additions to C=N Bonds and Nitriles

E. Kroon, T. Zarganes Tzitzikas, C. G. Neochoritis, and A. Dçmling

This chapter describes additions to imines and nitriles and their post-modifications within the context of domino reactions and multicomponent reaction chemistry.

Keywords: multicomponent...

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