Domino Reactions: Concepts for Efficient Organic Synthesis

647 Pages·2014·7.289 MB·English

by  Lutz F. Tietze

Editedby
LutzF.Tietze
DominoReactions
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Edited by Lutz F. Tietze
Domino Reactions
Concepts for Efficient Organic Synthesis
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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 DominoS /MichaelAdditionandRelatedReactions 106
N
4.2 DominoReactionsInitiatedbyNucleophilicRingOpeningof
Aziridines,Epoxides,andActivatedCyclopropanes 115
4.3 DominoS /BrookRearrangements 127
N
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