Rhodium catalysis in organic synthesis - methodsand reactions

686 Pages·2019·52.906 MB·English

by  TANAKA, KEN

RhodiumCatalysisinOrganicSynthesis

Rhodium Catalysis in Organic Synthesis
MethodsandReactions
Editedby
KenTanaka
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10 9 8 7 6 5 4 3 2 1
v
Contents
Preface xv
PartI Rhodium(I)Catalysis 1
1 Rhodium(I)-CatalyzedAsymmetricHydrogenation 3
TsuneoImamoto
1.1 Introduction 3
1.2 ChiralPhosphorusLigands 3
1.2.1 P-ChirogenicBisphosphineLigands 4
1.2.1.1 Electron-RichC SymmetricLigands 4
2
1.2.1.2 Three-HinderedQuadrantLigands 5
1.2.1.3 LigandsBearingTwoorThreeArylGroupsatthePhosphorus
Atom 5
1.2.2 DuPhos,BPE,andAnalogousLigands 6
1.2.3 Ferrocene-BasedBisphosphineLigands 7
1.2.4 C SymmetricTriaryl-orDiarylphosphineLigandswithAxial
2
Chirality 9
1.2.5 Phosphine–PhosphiteandPhosphine–PhosphoramideLigands 9
1.2.6 OtherBidentateLigands 9
1.2.7 MonodentatePhosphorusLigands 11
1.3 ApplicationofChiralPhosphorusLigandsinRhodium-Catalyzed
AsymmetricHydrogenation 12
1.3.1 HydrogenationofAlkenes 12
1.3.1.1 HydrogenationofEnamides 12
1.3.1.2 HydrogenationofEnolEsters 18
1.3.1.3 Hydrogenationofα,β-UnsaturatedAcids,Esters,andRelated
Substrates 19
1.3.1.4 HydrogenationofOtherFunctionalizedAlkenes 21
1.3.1.5 HydrogenationofUnfunctionalizedAlkenes 24
1.3.1.6 HydrogenationofHeteroarenes 24
1.3.2 HydrogenationofKetones 25
1.3.3 HydrogenationofImines,Oximes,andHydrazones 26
1.4 EnantioselectionMechanismofRhodium-CatalyzedAsymmetric
Hydrogenation 27
vi Contents
1.5 Conclusion 28
References 29
2 Rhodium(I)-CatalyzedHydroborationandDiboration 39
KoheiEndo
2.1 Introduction 39
2.2 HydroborationofAlkenes 39
2.2.1 DevelopmentofCatalystSystems 39
2.2.2 EnantioselectiveReactions 41
2.2.3 HydroborationofFunctionalizedMolecules 44
2.3 Diboration 45
2.3.1 1,1-DiborationReactions 45
2.3.2 1,2-DiborationReactions 45
2.4 Conclusion 46
References 47
3 Rhodium(I)-CatalyzedHydroformylationand
Hydroamination 49
ZhiweiChenandVyM.Dong
3.1 Introduction 49
3.2 Rhodium(I)-CatalyzedHydroformylation 49
3.2.1 AsymmetricHydroformylationofChallengingSubstrates 49
3.2.2 TransferHydroformylation 50
3.3 Rhodium(I)-CatalyzedHydroamination 54
3.3.1 AsymmetricRhodium(I)-CatalyzedHydroamination 54
3.3.2 Anti-MarkovnikovRhodium(I)-CatalyzedHydroamination 56
3.4 Conclusion 59
References 61
4 Rhodium(I)-CatalyzedHydroacylation 63
MaitaneFernándezandMichaelC.Willis
4.1 Introduction 63
4.2 Rhodium(I)-CatalyzedIntramolecularHydroacylation 63
4.2.1 SmallRingSynthesis:Five-MemberedRings 63
4.2.2 LargerRingSynthesis:Six-,Seven-,andEight-MemberedRings 66
4.3 Rhodium(I)-CatalyzedIntermolecularHydroacylation 68
4.3.1 N-BasedChelationControl 69
4.3.2 O-BasedChelationControl 70
4.3.3 S-BasedChelationControl 73
4.3.4 C=OasaDirectingGroupforHydroacylation 79
4.4 Conclusion 81
References 81
5 Rhodium(I)-CatalyzedAsymmetricAdditionofOrganometallic
ReagentstoUnsaturatedCompounds 85
Hsyueh-LiangWuandPing-YuWu
5.1 Introduction 85
Contents vii
5.2 α,β-UnsaturatedKetones 85
5.2.1 ChiralPhosphorusLigands 85
5.2.2 ChiralDieneLigands 89
5.2.3 ChiralBis-sulfoxideLigands 92
5.2.4 ChiralHybridLigands 92
5.3 α,β-UnsaturatedAldehydes 95
5.4 α,β-UnsaturatedEsters 98
5.5 α,β-UnsaturatedAmides 102
5.6 α,β-UnsaturatedPhosphonates 105
5.7 α,β-UnsaturatedSulfonylCompounds 105
5.8 NitroolefinCompounds 107
5.9 AlkenylheteroareneandAlkenylareneCompounds 111
5.10 Conclusion 111
References 112
6 Rhodium(I)-CatalyzedAllylationwithAlkynesand
Allenes 117
AdrianB.PritziusandBernhardBreit
6.1 Introduction 117
6.2 Rh(I)-CatalyzedAdditionofO-Nucleophiles 117
6.3 Rh(I)-CatalyzedAdditionofS-Nucleophiles 123
6.4 Rh(I)-CatalyzedAdditionofN-Nucleophiles 124
6.5 Rh(I)-CatalyzedAdditionofC-Nucleophiles 127
6.6 ApplicationofRhodium-CatalyzedAdditioninTotalSynthesis 127
6.7 Conclusion 129
References 130
7 Rhodium(I)-CatalyzedReductiveCarbon–CarbonBond
Formation 133
AdamD.J.CalowandJohnF.Bower
7.1 Introduction 133
7.2 Hydroformylation 133
7.2.1 DirectedRh-CatalyzedHydroformylation 134
7.2.2 ReversiblyBoundDirectingGroupsinRh-Catalyzed
Hydroformylation 135
7.3 ReductiveC—CBondFormationBetweenElectron-DeficientAlkenes
andCarbonylsorImines 137
7.3.1 ReductiveAldolReactions 137
7.3.2 ReductiveMannichReactions 142
7.4 ReductiveC—CBondFormationBetweenLessPolarized
Carbon-Basedπ-UnsaturatedSystemsandCarbonyls,Imines,or
Anhydrides 144
7.4.1 ReductiveC—CBondFormationsBetweenAlkenesandCarbonyls,
Imines,orAnhydrides 144
7.4.2 ReductiveC—CBondFormationsBetweenAlkynesandCarbonylsor
Imines 146
viii Contents
7.4.3 MiscellaneousProcesses 150
7.5 ReductiveC—CBondFormationBetweenCarbon-Based
π-UnsaturatedSystems 151
7.5.1 C—CBond-FormingReactionsBetweenAlkenesandAlkynes 151
7.5.2 C—CBond-FormingReactionsBetweenAlkynesandAlkynes 154
7.6 Conclusions 156
References 156
8 Rhodium(I)-Catalyzed[2+2+1]and[4+1]Cycloadditions 161
TsumoruMorimoto
8.1 Introduction 161
8.2 [2+2+1]Cycloaddition 161
8.2.1 [2+2+1]CycloadditionofanAlkyne,anAlkene,andCO
(Pauson–Khand-TypeReaction) 161
8.2.1.1 Pauson–Khand-TypeReactionUsingAldehydesasaC1
Component 162
8.2.1.2 Pauson–Khand-TypeReactionUsingFormatesasaC1
Component 171
8.2.1.3 Pauson–Khand-TypeReactionUsingOxalicAcidasaC1
Component 171
8.2.1.4 Pauson–Khand-TypeReactionUsingSupportedCarbon
Monoxide 172
8.2.2 [2+2+1]CycloadditionofTwoAlkynesandCO 172
8.2.3 Carbonylative[2+2+1]CycloadditionIncludinghetero-Multiple
Bonds 174
8.3 [4+1]Cycloaddition 176
8.3.1 CycloadditionofAllCarbon4π-ConjugatedSystemswithCO 176
8.3.2 Cycloadditionof4π-ConjugatedSystemsIncludingNitrogen
Atom 178
8.4 Conclusion 179
References 179
9 Rhodium(I)-Catalyzed[2+2+2]and[4+2]Cycloadditions 183
YuShibataandKenTanaka
9.1 Introduction 183
9.2 [2+2+2]Cycloaddition 183
9.2.1 [2+2+2]CycloadditionofAlkynes 184
9.2.2 [2+2+2]CycloadditionofAlkyneswithNitriles 199
9.2.3 [2+2+2]CycloadditionofAlkyneswithHeterocumulenes 200
9.2.4 [2+2+2]CycloadditionofAlkyneswithAlkenes 207
9.2.5 [2+2+2]CycloadditionofAlkyneswithCarbonylCompoundsand
Imines 211
9.3 [4+2]Cycloaddition 214
9.3.1 [4+2]CycloadditionofAlkyneswith1,3-Dienes 215
9.3.2 [4+2]CycloadditionviaC—HBondCleavage 218
9.4 Conclusion 222
References 225