Multicatalyst System in Asymmetric Catalysis

714 Pages·2014·48.25 MB·English

by  Jian Zhou

Multicatalyst
System in
Asymmetric
Catalysis
JIAN ZHOU

MULTICATALYST
SYSTEM IN
ASYMMETRIC
CATALYSIS
Dedicatedtomyfamily
MULTICATALYST
SYSTEM IN
ASYMMETRIC
CATALYSIS
JIANZHOU
ShanghaiKeyLaboratoryofGreenChemistryandChemicalProcesses
DepartmentofChemistry
EastChinaNormalUniversity
Shanghai,China
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LibraryofCongressCataloging-in-PublicationData:
Multicatalystsysteminasymmetriccatalysis/Dr.JianZhou,ShanghaiKeyLaboratoryofGreen
ChemistryandChemicalProcesses,DepartmentofChemistry,EastChinaNormalUniversity,Shanghai,
China.
pagescm
Includesindex.
ISBN978-1-118-07186-1(cloth)
1.Asymmetricsynthesis. 2.Catalysis. I.Zhou,Jian,1974-
QD262.Z462015
541′.395–dc23
2015017810
PrintedintheUnitedStatesofAmerica
10 9 8 7 6 5 4 3 2 1
CONTENTS
Preface xi
Contributors xiv
1 TowardIdealAsymmetricCatalysis 1
JianZhouandJin-ShengYu
1.1 Introduction, 1
1.2 ChallengestoRealizeIdealAsymmetricCatalysis, 7
1.3 Solutions, 13
1.4 BorrowIdeasfromNature, 22
1.5 Conclusion, 32
References, 32
2 MulticatalystSystem 37
Zhong-YanCao,FengZhu,andJianZhou
2.1 Introduction, 37
2.2 ModelsofSubstrateActivation, 42
2.2.1 TheActivationofElectrophiles, 43
2.2.2 TheActivationofNucleophiles, 54
2.2.3 SOMOCatalysis, 64
2.3 EarlyExamplesoftheApplicationofMulticatalystSystemin
AsymmetricCatalysis, 66
2.4 AGeneralIntroductionofMulticatalyst-PromotedAsymmetric
Reactions, 85
v
vi CONTENTS
2.5 ClassificationofMulticatalyst-PromotedAsymmetricReactions, 95
2.6 ChallengesandPossibleSolutions, 97
2.7 MulticatalystSystemVersusMultifunctionalCatalyst, 103
2.8 MulticatalystSystemVersusAdditives-EnhancedCatalysis, 105
2.9 Additive-EnhancedCatalysis, 107
2.9.1 Nitrogen-containingOrganobase, 109
2.9.2 InorganicBases, 111
2.9.3 H O, 114
2
2.9.4 MolecularSievesandDehydrators, 120
2.9.5 N-oxide,P-oxide,andAs-oxide, 125
2.9.6 AlcoholsandPhenols, 129
2.9.7 AmmoniumHalidesandMetalHalides, 133
2.9.8 Amides, 137
2.9.9 BrønstedAcidsandLewisAcids, 140
2.9.10 TwoorMoreAdditivesTogether, 144
2.10 Conclusion, 147
References, 148
3 AsymmetricMultifunctionalCatalysis 159
Jin-ShengYuand JianZhou
3.1 Introduction, 159
3.2 AsymmetricMultifunctionalOrganocatalysis, 164
3.2.1 H-BondDonor–TertiaryAmineCatalysis, 165
3.2.2 H-BondDonor–EnamineCatalysis, 193
3.2.3 H-BondDonor–PhaseTransferCatalysis, 203
3.2.4 H-BondDonor–TertiaryPhosphineCatalysis, 209
3.2.5 ChiralPhosphoricAcidCatalysis, 214
3.2.6 AsymmetricBifunctionalSaltCatalysis, 217
3.2.7 Miscellaneous, 222
3.3 AsymmetricHybridOrgano/MetalCatalysis, 227
3.3.1 BrønstedBase/LewisAcidBifunctionalCatalysis, 228
3.3.2 LewisBase/LewisAcidBifunctionalCatalysis, 233
3.3.3 BrønstedAcid/LewisAcidBifunctionalCatalysis, 236
3.3.4 Enamine/LewisAcidBifunctionalCatalysis, 238
3.3.5 HemilableTrisoxazolines, 240
3.4 AsymmetricMultifunctionalMultimetallicCatalysis, 242
3.4.1 AsymmetricMultifunctionalHeteromultimetallic
Catalysis, 243
3.4.2 AsymmetricMultifunctionalHomomultimetallic
Catalysis, 251
3.5 Anion-EnabledBifunctionalAsymmetricCatalysis, 259
3.5.1 AmmoniumFluoridesorMetalFluorides, 262
3.5.2 MetalPhosphates, 265
3.5.3 MetalCarboxylates, 265
CONTENTS vii
3.5.4 AmmoniumorMetalAryloxides, 269
3.5.5 HydroxidesandAlkoxides, 271
3.5.6 MetalAmides, 276
3.6 Conclusion, 277
References, 277
4 AsymmetricCooperativeCatalysis 291
LongChen,Yun-LinLiu,andJianZhou
4.1 Introduction, 291
4.2 CatalyticAsymmetricMichaelAdditionReaction, 292
4.2.1 CombiningMultipleMetalCatalysts, 292
4.2.2 CombiningTwoDistinctOrganocatalysts, 293
4.2.3 CombiningMetalCatalystwithOrganocatalyst, 297
4.3 CatalyticAsymmetricMannichReaction, 299
4.3.1 CombiningLewisAcidCatalystandBrønstedBase
Catalyst, 300
4.3.2 CombiningBrønstedAcidCatalystandLewisAcid
Catalyst, 301
4.3.3 CombiningBrønstedAcidCatalystandSecondary
AmineCatalyst, 303
4.4 CatalyticAsymmetricConia-EneReaction, 304
4.4.1 CombiningChiralLewisAcidandAchiralLewisAcid, 304
4.4.2 CombiningChiralBrønstedBaseandAchiralLewisAcid, 306
4.5 CatalyticAsymmetricUmpolungReaction, 307
4.5.1 CombiningNHCCatalystandLewisAcidCatalyst, 307
4.5.2 CombiningNHCCatalystandBrønstedAcidCatalyst, 313
4.6 CatalyticAsymmetricCyanosilylationReaction, 315
4.7 α-AlkylationReactionofCarbonylCompounds, 317
4.7.1 α-AlkylationofCarbonylCompoundsusingAlcohols
asAlkylationReagents, 317
4.7.2 α-AlkylationofCarbonylCompoundsthroughBenzylic
C HBondOxidation, 325
4.8 CatalyticAsymmetricAllylicAlkylationReaction, 326
4.8.1 CombiningAchiralTransitionMetalwithChiral
LUMO-LoweringCatalysis, 327
4.8.2 CombiningChiralTransitionMetalCatalysiswith
AchiralOrganocatalyst, 331
4.9 CatalyticAsymmetricAldol-TypeReaction, 335
4.10 CatalyticAsymmetric(Aza)-Morita–Baylis–HillmanReaction, 338
4.10.1 ChiralLewisBase/AchiralAcidCocatalyzed
(aza)-MBHReaction, 341
4.10.2 AchiralLewisBase/ChiralAcidCocatalyzed
(aza)-MBHReaction, 342
4.11 CatalyticAsymmetricHydrogenationReaction, 346
viii CONTENTS
4.12 CatalyticAsymmetricCycloadditionReaction, 350
4.12.1 [2+2]Reaction, 351
4.12.2 [4+2]Reaction, 352
4.13 CatalyticAsymmetricN HInsertionReaction, 356
4.14 CatalyticAsymmetricα-FunctionalizationofAldehydes, 358
4.15 MiscellaneousReaction, 360
4.16 Conclusion, 364
References, 365
5 AsymmetricDoubleActivationCatalysisbyMulticatalystSystem 373
LongChen,Zhong-YanCao,andJianZhou
5.1 Introduction, 373
5.2 DoubleActivationbyAminocatalysisandLewisBaseCatalysis, 374
5.3 AsymmetricDoublePrimaryAmineandBrønstedAcidCatalysis, 378
5.3.1 Diels–Alder(DA)Reaction, 379
5.3.2 MichaelAddition, 379
5.3.3 Epoxidation, 386
5.3.4 MiscellaneousReaction, 390
5.4 AsymmetricDoubleMetalandBrønstedBaseCatalysis, 391
5.4.1 [3+2]Cycloaddition, 392
5.4.2 AldolReaction, 396
5.4.3 MiscellaneousReactions, 399
5.5 AsymmetricH-BondDonorCatalysisandLewisBaseCatalysis, 401
5.6 SequentialDoubleActivationCatalysis, 404
5.7 Conclusion, 408
References, 408
6 AsymmetricAssistedCatalysisbyMulticatalystSystem 411
Xing-PingZengandJianZhou
6.1 Introduction, 411
6.2 AsymmetricAssistedCatalysiswithinAcidsandBases, 414
6.2.1 AcidAssistedAcidCatalysis, 415
6.2.2 BaseAssistedBrønstedAcidCatalysis, 433
6.2.3 LewisBaseAssistedBrønstedBaseCatalysis, 435
6.2.4 AcidAssistedBaseCatalysis, 437
6.2.5 Miscellaneous, 439
6.3 ModulationofaMetalComplexbyaChiralLigand, 443
6.3.1 ModulationofaChiralMetalComplexwithaChiral
Ligand, 444
6.3.2 AsymmetricDeactivation,Activation,and
Deactivation/Activation, 451
6.3.3 AsymmetricActivationofRacemicCatalystsBearing
TroposLigand, 460