Domino Reactions: Concepts for Efficient Organic Synthesis

638 Pages·2016·3.93 MB·English

by  Tietze L.F. (Ed.)

Editedby
LutzF.Tietze
DominoReactions
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Domino Reactions
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V
Contents
Preface XIII
ListofContributors XV
ListofAbbreviations XIX
Introduction 1
References 4
1 Transition-Metal-CatalyzedCarbonylativeDominoReactions 7
Xiao-FengWu,HelfriedNeumann,andMatthiasBeller
1.1 Introduction 7
1.2 Transition-Metal-CatalyzedCarbonylativeDominoReactions 8
1.2.1 Ruthenium-CatalyzedCarbonylativeDominoReactions 8
1.2.2 Rhodium-CatalyzedCarbonylativeDominoReactions 13
1.2.3 Palladium-CatalyzedCarbonylativeDominoReactions 16
1.2.4 Iron-,Copper-,Nickel-,andCobalt-CatalyzedCarbonylativeDomino
Reactions 24
1.3 Outlook 27
References 27
2 MetathesisReactionsinDominoProcesses 31
KamalM.DawoodandPeterMetz
2.1 DominoProcessesFeaturingSolelyMetathesisEvents 31
2.1.1 ReactionsInvolvingOnlyAlkenes 31
2.1.2 ReactionsInvolvingAlkenesandAlkynes 41
2.2 DominoProcessesFeaturingMetathesisandNon-metathesis
Events 52
2.2.1 Metathesis/RedoxTransformation 52
2.2.2 Metathesis/Isomerization 53
2.2.3 Metathesis/Cycloaddition 56
2.2.4 Metathesis/Substitution 58
2.2.5 Metathesis/ConjugateAddition 59
2.2.6 Metathesis/CarbonylOlefination 62
VI Contents
2.3 ConclusionandOutlook 63
Acknowledgments 63
References 63
3 C–HActivationReactionsinDominoProcesses 67
GavinChitTsuiandMarkLautens
3.1 HeckReactions/C–HActivations 67
3.2 CarbopalladationsandAminopalladationsofAlkynes/C–H
Activations 72
3.3 Palladium-Catalyzed/Norbornene-MediatedorthoC–HActivations 80
3.4 DominoReactionsInvolvingHeteroatom-DirectedC–H
Activations 96
3.5 Conclusions 101
References 101
4 DominoReactionsInitiatedbyNucleophilicSubstitution 105
HiriyakkanavarIla,AnandAcharya,andSaravananPeruncheralathan
4.1 DominoSN/MichaelAdditionandRelatedReactions 106
4.2 DominoReactionsInitiatedbyNucleophilicRingOpeningof
Aziridines,Epoxides,andActivatedCyclopropanes 115
4.3 DominoSN/BrookRearrangements 127
References 138
5 RadicalReactionsinDominoProcesses 141
GuanghuiAnandGuigenLi
5.1 Introduction 141
5.2 Radical/CationDominoProcesses 143
5.3 Radical/AnionicDominoProcesses 148
5.4 DominoRadical/RadicalProcess 154
5.5 Radical/PericyclicDominoProcesses 172
5.6 AsymmetricRadicalDominoProcesses 174
5.6.1 ChiralAuxiliary-DirectedAsymmetricRadicalDominoProcesses 174
5.6.2 ChiralCatalyst-DrivenAsymmetricRadicalDominoProcesses 176
5.7 ConclusionandOutlook 178
Acknowledgments 179
References 179
6 PericyclicReactionsinDominoProcesses 183
LukasJ.PatalagandDanielB.Werz
6.1 Introduction 183
6.2 Cycloadditions 184
6.2.1 Cycloaddition/Cycloaddition 184
6.2.2 Cycloaddition/Cycloreversion 185
6.2.3 Cycloaddition/SigmatropicRearrangement 188
6.2.4 Cycloaddition/Electrocyclization 189
Contents VII
6.2.5 Cycloaddition/MixedTransformations 191
6.3 SigmatropicRearrangements 192
6.3.1 SigmatropicRearrangement/SigmatropicRearrangement 192
6.3.2 SigmatropicRearrangement/Cycloaddition 195
6.3.3 SigmatropicRearrangement/Electrocyclization 196
6.3.4 SigmatropicRearrangement/MixedTransformations 199
6.4 Electrocyclizations 201
6.4.1 Electrocyclization/Electrocyclization 201
6.4.2 Electrocyclization/Cycloaddition 202
6.4.3 Electrocyclization/SigmatropicRearrangement 205
6.4.4 Electrocyclization/MixedTransformations 208
6.5 MixedTransformations 209
6.5.1 MixedTransformationsFollowedbyPericyclicReactions 209
6.5.2 CascadesofCarbopalladationsFollowedbyPericyclicReactions 211
6.5.3 DominoKnoevenagel/HeteroDiels–AlderReaction 214
6.6 ConcludingRemarks 214
Acknowledgments 215
References 215
7 ModernDominoReactionsContainingaMichaelAdditionReaction 219
ScottG.Stewart
7.1 Introduction 219
7.2 FormationofAcyclicProducts 221
7.3 FormationofCarbocycles 225
7.4 Formationof O-Heterocycles 236
7.5 Formationof N-Heterocycles 250
7.6 Formationof S-Heterocycles 257
7.7 FormationofHeterocyclesContainingNitrogenandOxygen 260
References 262
8 AldolReactionsinDominoProcesses 267
ChristophSchneiderandMichaelBoomhoff
8.1 Introduction 267
8.2 DominoProcesseswiththeAldolReactionasFirstStep 267
8.2.1 Aldol-LactonizationReactions 267
8.2.2 Aldol/PrinsReactions 270
8.2.3 Aldol/AcetalizationReactions 272
8.2.4 Aldol–TishchenkoReactions 273
8.2.5 VinylogousAldol/MichaelReactions 276
8.3 DominoProcesseswiththeAldolReactionasSubsequentStep 277
8.3.1 ConjugateAddition/AldolReactions 277
8.3.1.1 AdditionofCarbonNucleophiles 277
8.3.1.2 AdditionofSulfurNucleophiles 281
8.3.1.3 AdditionofOxygenandNitrogenNucleophiles 283
8.3.1.4 Iodo-AldolReactions 285
VIII Contents
8.3.1.5 ReductiveAldolReactions 287
8.3.2 Isomerization/AldolReactions 289
8.3.3 WittigRearrangement/AldolReactions 290
8.3.4 Cycloaddition/AldolReactions 290
8.4 ConclusionandOutlook 292
References 292
9 OxidationsandReductionsinDominoProcesses 295
GovindasamySekar,IyyanarKarthikeyan,andDhandapaniGanapathy
9.1 Introduction 295
9.2 DominoReactionsInitiatedbyOxidationorReductionReaction 296
9.2.1 DominoReactionsInitiatedbyanOxidationReaction 296
9.2.2 DominoReactionsInitiatedbyReductionReaction 301
9.3 DominoReactionsHavingOxidationinMiddleoftheSequence 312
9.4 DominoReactionsTerminatedbyOxidationorReduction
Reaction 313
9.4.1 DominoReactionsTerminatedbyOxidationReaction 313
9.4.2 DominoReactionsTerminatedbyReductionReaction 314
9.5 Conclusion 319
Acknowledgments 319
References 319
10 OrganocatalysisinDominoProcesses 325
He´le`nePellissier
10.1 Introduction 325
10.2 One-andTwo-ComponentDominoReactions 326
10.2.1 DominoReactionsInitiatedbytheMichaelReaction 327
10.2.1.1 DominoMichael/MichaelReactions 327
10.2.1.2 DominoMichael/AldolReactions 334
10.2.1.3 DominoMichael/IntramolecularHeterocyclizationReactions 340
10.2.1.4 DominoMichael/IntramolecularAlkylationReactions 349
10.2.1.5 DominoMichael/(aza)–HenryReactions 352
10.2.1.6 DominoMichael/KnoevenagelReactions 355
10.2.1.7 DominoMichael/aza-Morita–Baylis–HillmanReactions 357
10.2.1.8 DominoMichael/MannichReactions 357
10.2.1.9 OtherDominoReactionsInitiatedbytheMichaelReaction 359
10.2.2 DominoReactionsInitiatedbyOtherReactions 361
10.2.2.1 DominoReactionsInitiatedbytheIndirectMannichReaction 361
10.2.2.2 DominoReactionsInitiatedbythe(Aza)-Morita–Baylis–Hillman
Reaction 363
10.2.2.3 DominoReactionsInitiatedbytheFriedel–CraftsReaction 364
10.2.2.4 MiscellaneousDominoReactions 365
10.3 MulticomponentReactions 371
10.3.1 MulticomponentReactionsInitiatedbytheMichaelReaction 371
10.3.1.1 MichaelReactionsofα,β-UnsaturatedAldehydes 371
Contents IX
10.3.1.2 MichaelReactionsofOtherα,β-UnsaturatedCarbonyl
Compounds 378
10.3.1.3 MichaelReactionsofNitroolefins 380
10.3.2 MulticomponentReactionsInitiatedbytheKnoevenagelReaction 385
10.3.3 MulticomponentReactionsBasedontheMannichReaction 388
10.3.4 MulticomponentReactionsBasedontheBiginelliReaction 392
10.3.5 MulticomponentReactionsBasedontheHantzschReaction 394
10.3.6 MulticomponentReactionsBasedontheStreckerReaction 395
10.3.7 MulticomponentReactionsBasedonthePetasisReaction 397
10.3.8 1,3-DipolarCycloaddition-BasedMulticomponentReactions 398
10.3.9 MiscellaneousMulticomponentReactions 400
10.4 Conclusions 405
References 405
11 Metal-CatalyzedEnantio-andDiastereoselectiveC–CBond-Forming
ReactionsinDominoProcesses 419
ShinobuTakizawaandHiroakiSasai
11.1 DominoReactionInitiatedbyC–CBondFormation 419
11.1.1 DominoReactionInitiatedbyConjugateAddition 419
11.1.2 DominoReactionInitiatedbyCycloaddition 433
11.1.3 DominoReactionInitiatedbyCarbometalation 435
11.2 DominoReactionInitiatedbyC–HBondFormation 435
11.2.1 DominoReactionInitiatedbyConjugateAddition 435
11.3 DominoReactionInitiatedbyC–NBondFormation 442
11.3.1 DominoReactionInitiatedbyImineFormation 442
11.3.2 DominoReactionBasedonCycloaddition 443
11.4 DominoReactionInitiatedbyC–OBondFormation 445
11.4.1 DominoReactionInitiatedbyCarbonylYlideFormation 445
11.4.2 DominoReactionInitiatedbyOxoniumYlideFormation 450
11.4.3 DominoReactionBasedonCycloaddition 452
11.4.4 DominoReactionBasedonPd(II)/Pd(IV)Catalysis 454
11.4.5 DominoReactionBasedonaWackerOxidation 454
11.5 DominoReactionInitiatedbyC–BandC–SiBondFormation 455
11.5.1 DominoReactionInitiatedbyConjugateAddition 456
11.6 ConclusionandOutlook 457
References 458
12 DominoProcessesunderMicrowaveIrradiation,HighPressure,andin
Water 463
BoJiang,Shu-JiangTu,andGuigenLi
12.1 Introduction 463
12.2 Microwave-AssistedDominoReactions 464
12.2.1 IntramolecularDominoReactionsunderMicrowaveHeating 464
12.2.2 Two-ComponentDominoReactionunderMicrowaveHeating 465
12.2.3 MulticomponentDominoReactionsunderMicrowaveHeating 472