Asymmetric Hydrogenation and Transfer Hydrogenation

393 Pages·2021·12.96 MB·english

by  Virginie Ratovelomanana-Vidal

AsymmetricHydrogenationandTransferHydrogenation
Asymmetric Hydrogenation and Transfer
Hydrogenation
Edited by
Virginie Ratovelomanana-Vidal
Phannarath Phansavath
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v
Contents
Foreword xi
Preface xiii
1 TheHistoricalDevelopmentofAsymmetricHydrogenation 1
JohnM.Brown
1.1 Introduction 1
1.2 EarlyWorkontheRecognitionofMolecularAsymmetry 1
1.3 OriginsandEarlyDevelopmentofAsymmetricSynthesis 4
1.4 EarlyDevelopmentsintheAsymmetricHeterogeneousHydrogenation
ofAlkenes 8
1.5 TheDevelopmentofRhodiumAsymmetricHomogeneous
HydrogenationofAlkenes 10
1.6 TheDevelopmentofRutheniumAsymmetricHomogeneous
HydrogenationofAlkenes 16
1.7 Conclusions 18
References 19
2 Asymmetric(Transfer)HydrogenationofFunctionalized
AlkenesDuringthePastDecade 25
ChristianBruneau
2.1 Introduction 25
2.2 AsymmetricHydrogenationwithRhodiumCatalysts 25
2.2.1 ChiralBisphosphineLigands 25
2.2.2 ChiralFerrocenylBisphosphineLigands 27
2.2.3 ChiralPhosphine–PhosphoramiditeandPhosphine–Phosphite
Ligands 31
2.2.4 Self-assembledDiphosphineLigands 33
2.2.5 MonodentatePhosphorusLigands 33
2.2.6 AsymmetricTransferHydrogenationwithRhodiumCatalysts 34
2.3 AsymmetricHydrogenationwithIridiumCatalysts 36
2.3.1 ChiralBidentateFerrocenylLigands 36
2.3.2 OtherChiralBidentateP,N-ligands 37
2.3.3 AsymmetricTransferHydrogenationwithIridiumCatalysts 42
vi Contents
2.4 AsymmetricHydrogenationwithOtherTransitionMetalCatalysts 43
2.4.1 AsymmetricHydrogenationwithRutheniumCatalysts 43
2.4.2 AsymmetricHydrogenationwithPalladiumCatalysts 46
2.5 Asymmetric(Transfer)HydrogenationwithFirst-rowTransitionMetal
Catalysts 48
2.6 Conclusion 48
References 49
3 Asymmetric(Transfer)HydrogenationofFunctionalized
Ketones 55
NoriyoshiAraiandTakeshiOhkuma
3.1 Introduction 55
3.2 Asymmetric(Transfer)HydrogenationofAlkylKetones 57
3.3 AsymmetricHydrogenationofα,β-UnsaturatedKetones 66
3.3.1 AlkenylAlkylKetones 66
3.3.2 AlkynylAlkylKetones 71
3.4 AsymmetricHydrogenationofα-Aminoketones 73
3.5 AsymmetricHydrogenationofα-hydroxyketones 77
3.6 AsymmetricHydrogenationofα-Oxophosphonates 80
3.7 SummaryandConclusions 83
References 83
4 Asymmetric(Transfer)HydrogenationofArylandHeteroaryl
Ketones 87
Jian-HuaXieandQi-LinZhou
4.1 Introduction 87
4.2 AsymmetricHydrogenationofArylandHeteroarylKetones 88
4.2.1 ChiralRutheniumCatalysts 90
4.2.1.1 ChiralRuthenium-Diphosphine/DiamineCatalysts 90
4.2.1.2 ChiralArene–Ruthenium-DiamineCatalysts 95
4.2.1.3 ChiralRuthenium–Phosphine–OxazolineCatalysts 96
4.2.1.4 ChiralRutheniumCatalystsContainingTridentatePincerLigands 97
4.2.1.5 ChiralRutheniumCatalystsContainingTetradentateLigands 98
4.2.2 ChiralIridiumCatalysts 98
4.2.3 OtherChiralMetalCatalysts 100
4.3 AsymmetricTransferHydrogenationofArylandHeteroaryl
Ketones 103
4.3.1 ChiralRutheniumCatalysts 104
4.3.1.1 ChiralAreneRuthenium–N-Sulfonylated1,2-DiamineComplexes 104
4.3.1.2 ChiralRutheniumCatalystswithOtherBidentateLigands 107
4.3.1.3 ChiralRutheniumCatalystsContainingTridentateandTetradentate
Ligands 111
4.3.2 ChiralRhodiumandIridiumCatalysts 112
4.3.2.1 ChiralRhodiumandIridiumComplexesContainingDiamineand
RelatedLigands 113
Contents vii
4.3.2.2 ChiralRhodiumandIridiumCatalystsContainingOtherLigands 116
4.3.3 OtherChiralMetalCatalysts 117
4.3.3.1 ChiralIronCatalysts 118
4.3.3.2 ChiralOsmiumCatalysts 119
4.3.3.3 OtherChiralMetalCatalysts 119
4.4 Summary 120
References 121
5 Asymmetric(Transfer)HydrogenationofSubstitutedKetones
ThroughDynamicKineticResolution 129
Pierre-GeorgesEcheverria,TaharAyad,PhannarathPhansavathandVirginie
Ratovelomanana-Vidal
5.1 Introduction 129
5.2 α-SubstitutedKetones 130
5.3 α-SubstitutedCyclicKetones 135
5.4 α,α′-DisubstitutedCyclicKetones 142
5.5 α,β-DisubstitutedCyclicKetones 143
5.6 α-Substitutedβ-KetoEsters 144
5.6.1 α-Aminoβ-KetoEsters 144
5.6.2 Otherα-Substitutedβ-KetoEsters 151
5.7 α-Substitutedβ-KetoAmides 156
5.8 α-Substitutedβ-KetoSulfones,Sulfonamides,andPhosphonates 160
5.9 β-Substitutedα-KetoEstersandPhosphonates 163
5.10 β-AlkoxyKetones 166
5.11 1,2-Diketones 167
5.12 β-SubstitutedKetones 167
5.13 α-SubstitutedAldehydes 168
5.14 SummaryandConclusions 169
References 169
6 IndustrialApplicationsofAsymmetric(Transfer)
Hydrogenation 175
XumuZhangandPan-LinShao
6.1 Introduction 175
6.2 IndustrialApplicationsofAsymmetricHydrogenation 177
6.2.1 AsymmetricHydrogenationofEnamide 177
6.2.1.1 L-DOPA 177
6.2.1.2 Ramipril 178
6.2.1.3 Sitagliptin 179
6.2.1.4 (R)-3-Amino-1-butanol 181
6.2.1.5 (S)-2,6-Dimethyltyrosine 182
6.2.1.6 Apremilast 184
6.2.2 AsymmetricHydrogenationofKetone 185
6.2.2.1 Duloxetine 185
6.2.2.2 Dorzolamide 186
viii Contents
6.2.2.3 (R)-1-(3,5-Bis(trifluoromethyl)-phenyl)ethanol 187
6.2.2.4 4-AA(KeyIntermediatetoCarbapenemAntibiotics) 189
6.2.2.5 Rivastigmine 190
6.2.2.6 Montelukast 191
6.2.2.7 Crizotinib 192
6.2.2.8 (R)-Phenylephrine 194
6.2.2.9 AtorvastatinCalciumSalt 197
6.2.2.10 Orlistat 198
6.2.2.11 Ezetimibe 199
6.2.3 AsymmetricHydrogenationofOlefin 201
6.2.3.1 L-Menthol 201
6.2.3.2 Sacubitril 202
6.2.3.3 Naproxen,Ibuprofen,andFlurbiprofen 204
6.2.3.4 Ramelteon 205
6.2.3.5 Aliskiren 205
6.2.3.6 (+)-cis-MethylDihydrojasmonate 207
6.2.4 AsymmetricHydrogenationofImine 209
6.2.4.1 Solifenacin 209
6.2.4.2 (S)-Metolachlor 210
6.2.5 AsymmetricTransferHydrogenation 211
6.3 SummaryandConclusions 212
References 212
7 TetheredRuthenium(II)CatalystsinAsymmetricTransfer
Hydrogenation 221
VijyeshK.Vyas,RichardC.KnightonandMartinWills
7.1 Introduction:TheRationaleBehindTetheredCatalystsDesign 221
7.2 TetheredRu(II)CatalystsandTheirSyntheses 222
7.2.1 SyntheticApproachestoTetheredCatalysts 224
7.3 ApplicationstoAsymmetricReductionsofKetonesandImines 226
7.3.1 ReductionsofAcetophenoneDerivatives 226
7.3.1.1 AsymmetricTransferHydrogenationUsingFormicAcid 228
7.3.1.2 ReductionUnderAqueousConditions 231
7.3.1.3 HydrogenationwithHydrogenGas 232
7.3.1.4 RacemicCatalystsforReductions 232
7.3.1.5 SpecificApplicationstoComplexAcetophenoneDerivatives 232
7.3.2 ReductionsofAcetylenicKetones 235
7.3.3 ReductionsofBenzophenoneKetones 235
7.3.4 ReductionsofDiverseKetones 237
7.3.5 DynamicKineticResolutions 242
7.3.6 ReductionsofImines 247
7.4 ConclusionsandOutlook 248
References 249
Contents ix
8 HomogeneousAsymmetricHydrogenationofHeteroaromatic
CompoundsCatalyzedbyTransitionMetalComplexes 255
Qing-HuaFan,Yan-MeiHeandFa-JuLi
8.1 Introduction 255
8.2 AsymmetricHydrogenationofQuinolines 257
8.3 AsymmetricHydrogenationofQuinoxalines 260
8.4 AsymmetricHydrogenationofIsoquinolines 262
8.5 AsymmetricHydrogenationofPyridinesandPyrazines 263
8.6 AsymmetricHydrogenationofIndolesandPyrroles 265
8.7 AsymmetricHydrogenationofHeteroareneswith
Multi-N-Heterocycles 268
8.8 AsymmetricHydrogenationofOtherN-Heteroarenes 270
8.9 AsymmetricHydrogenationofO-andS-Heteroarenes 273
8.10 SummaryandConclusions 275
Acknowledgments 276
References 276
9 Asymmetric(Transfer)HydrogenationofImines 281
ItziarPeñafiel,JuanMangas-SánchezandCarmenClaver
9.1 AsymmetricHydrogenationofImines 281
9.1.1 IridiumCatalysts 281
9.1.1.1 (P,P)Ligands 281
9.1.1.2 (P,N)Ligands 282
9.1.1.3 P-MonodentateLigands 286
9.1.2 RhodiumandPalladiumCatalysts 287
9.2 AsymmetricTransferHydrogenationofImines 288
9.2.1 RutheniumCatalysts 289
9.2.2 IridiumandRhodiumCatalysts 290
9.2.3 IronCatalysts 290
9.3 NewApproaches 292
9.3.1 MetalFree 292
9.3.2 BiocatalyticImineReduction 293
9.3.2.1 ArtificialMetalloenzymes 294
9.3.2.2 ImineReductases(IREDs) 297
9.4 SummaryandConclusions 301
References 301
10 AsymmetricHydrogenationinContinuous-Flow
Conditions 307
GergelyFarkas,JózsefMadarászandJózsefBakos
10.1 Introduction 307
10.2 ChirallyModifiedMetalSurfaces 308
10.3 Well-definedTransition-metalComplexes 314
x Contents
10.3.1 ImmobilizedSystems 315
10.3.1.1 CovalentlyAnchoredLigands 315
10.3.1.2 ImmobilizationbytheAugustineMethod 316
10.3.1.3 IonicLiquidsasMatricesforTransition-metalComplexCatalysts 321
10.3.2 HomogeneousSystems 325
10.3.3 Self-supportedSystems 328
10.4 Organocatalysts 329
10.5 ChiralAuxiliary-controlledAsymmetricHydrogenationinFlow 332
10.6 SummaryandOutlook 333
References 333
11 OrganocatalyticAsymmetricTransferHydrogenation
Reactions 339
SayantaniDas,VijayN.WakchaureandBenjaminList
11.1 Introduction 339
11.2 ReductionofC=CDoubleBonds 341
11.3 ReductionofC=NDoubleBonds 347
11.4 CascadeReactions 359
11.5 Dearomatization 365
11.6 Conclusions 369
References 369
Index 375
xi
Foreword
It is a tremendous honor and a sheer delight to have been asked to write an
introductionforthisimportantandtimelytomeentitled“AsymmetricHydrogena-
tionandTransferHydrogenation,”editedbymydearfriendsDr.VirginieVidaland
Dr. Phannarath (Poki) Phansavath, themselves notable contributors to the field.
Thisbookwillcertainlystandasalandmarkcontributionthatnotonlysummarizes
thestateofthecurrentartforthisusefulreactiongenrebutalsosetsthestagefor
practitionerstoexplorevistasoffutureimportance.
As many readers will recognize, (transfer) hydrogenation has a very long and
distinguishedhistoryinorganicchemistry,playingakeyroleinthefieldandindeed
perhaps serving as a bellwether for the development of synthetic methods in the
disciplineasawhole.PaulSabatier(NobelPrize,1912)hasbeencreditedwiththe
first advances in alkene hydrogenation in the late 1890s, and it was Knoevenagel
who reported the first transfer hydrogenation reaction in 1903 – essentially a
dimerization process involving disproportionation between identical donor and
acceptor units promoted by palladium black in a heterogeneous transformation.
Two decades later (1925) came the famous Meerwein–Ponndorf–Verley reaction,
a redox coupling between a different donor and acceptor. Several more decades
passed (1960s) before homogeneous transition metal catalysts were developed
for both hydrogenation (e.g. Wilkinson’s catalyst) and transfer hydrogenation,
whereHenbest,Mitchell,andcoworkershydrogenatedcarbonylstoalcoholsusing
isopropanol as the hydride transfer reagent. This was subsequently followed by
transition metal-catalyzed asymmetric processes for carbonyl, imine, alkene, and
related reductions, in which the seminal work of Henri Kagan culminated in the
awardoftheNobelPrizeinChemistrytoNoyoriandKnowlesfortheircontribution
to the field in 2001. Thus began the explosive flurry of activity, leading to the
current status of the field – a cluster of reactions that occupies an exalted status
within the discipline owing to the fact that they are being used in the fragrance,
flavors, pharmaceutical, and agrochemical industries worldwide on ton scale.
Flowtechniques,biocatalysis,andorganocatalyticmethodsroundoutmorerecent
additions to the armamentarium available to practitioners of the art of organic
synthesis,pointingtoexcitingopportunitiesforfurtherexploration.
Homogeneous catalytic asymmetric (transfer) hydrogenation transformations
thus quite rightfully deserve the attention they are receiving in this volume. As