Asymmetric Bronsted Acid Catalysis

243 Pages·2016·1.65 MB·English

by  Magnus Rueping

MagnusRueping
DixitParmar
ErliSugiono
AsymmetricBrønstedAcidCatalysis
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MagnusRueping,DixitParmar,andErliSugiono
Asymmetric Brønsted Acid Catalysis
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V
Contents
Preface IX
1 Introduction 1
1.1 BookStructureandNotation 1
1.2 CatalystPreparation 2
1.3 MetalImpurities 3
References 3
2 ReactionsofImines 5
2.1 NucleophilicAdditionReactions 5
2.1.1 C-Nucleophiles 5
2.1.2 N-Nucleophiles 17
2.1.3 O-Nucleophiles 20
2.1.4 P-Nucleophiles 21
2.2 MannichReactions 24
2.3 StreckerReactions 28
2.4 BiginelliReactions 31
2.5 Friedel–CraftsReactions 33
2.5.1 IndoleCouplingPartnerswithAldimines 33
2.5.2 IndoleCouplingPartnerstoKetimines 35
2.5.3 Non-IndoleAromaticPartners 38
2.5.4 Pictet–SpenglerReactions 41
2.6 TransferHydrogenations 44
2.6.1 IminePartners 44
2.6.2 α-IminoEsterPartners 49
2.6.3 N-Heterocycles 51
2.6.4 CascadeProcesses 56
2.6.5 MiscellaneousReactions 61
2.7 PericyclicReactions 63
2.7.1 Aza-Diels–Alder/Povarov 63
2.7.2 1,3-DipolarCycloaddition 69
VI Contents
2.7.3 ElectrocyclizationsandSigmatropicRearrangements 72
2.8 RadicalReactions 77
References 79
3 ReactionsofGeneratedImineIntermediates 87
3.1 Enamines 87
3.1.1 NucleophilicAdditionReactions 87
3.1.2 TransferHydrogenation 90
3.2 IndolesContainingLeavingGroups 91
3.2.1 NucleophilicAdditionReactions 92
3.2.2 Friedel–CraftsReactions 96
3.3 N-AcetalsandAminals 99
3.3.1 NucleophilicAdditionReactions 99
3.3.2 Friedel–CraftsReactions 104
3.3.3 TransferHydrogenation 105
3.4 MiscellaneousFormation 111
References 115
4 ReactionsofCarbonyls 117
4.1 NucleophilicAdditionReactions 117
4.1.1 C-Nucleophiles 117
4.1.2 N-,O-,andP-Nucleophiles 124
4.2 AldolReactions 133
4.3 PericyclicReactions 137
4.4 Reductions 140
References 142
5 ReactionsofGeneratedCarbonylIntermediates 145
5.1 EnolEthers 145
5.2 Acetals 149
5.3 PhenolsContainingLeavingGroups 153
References 158
6 ReactionsofAlkenes 161
6.1 NucleophilicAdditionReactions 161
6.2 Friedel–CraftsReactions 169
6.3 PericyclicReactions 172
6.4 Cascades 177
References 180
7 ReactionsofOtherSubstrates 183
7.1 Aziridines 183
7.2 O-HeterocyclesandEthers 185
7.3 HydrazinesandHydrazones 190
7.4 Azo/DiazoSubstrates 192
Contents VII
7.5 Halogens 198
7.5.1 Fluorine 198
7.5.2 Bromine 203
7.6 OxidizingAgents 206
7.7 MiscellaneousSubstrates 209
References 212
ExperimentalProtocols 215
AppendixA:CatalystFrequency 215
AppendixB:OverviewofPhosphoricAcids(PA) 217
AppendixC:OverviewofN-PhosphoramideAcids(NPA) 221
AppendixD:OverviewofSPINOLPhosphoricAcids(SPA) 223
AppendixE:OverviewofAllOtherBrønstedAcids(BA) 225
Index 229