Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis

547 Pages·2009·13.73 MB·English

by  Choong Eui Song

Cinchona Alkaloids in
Synthesis and Catalysis
Edited by
Choong Eui Song
Further Reading
Crabtree, R.H.(ed.) Stepnicka, P.(ed.)
Handbook of Green Chemistry Ferrocenes
- Green Catalysis Ligands,MaterialsandBiomolecules
2009 Hardcover
Hardcover ISBN:978-0-470-03585-6
ISBN:978-3-527-31577-2
Christmann, M.,Bräse, S.(eds.)
Kollár,L(ed.)
Asymmetric Synthesis -
Modern Carbonylation
The Essentials
Methods
2008
2008 Softcover
Hardcover ISBN:978-3-527-32093-6
ISBN:978-3-527-31896-4
Hudlicky,T., Reed,J. W.
Börner,A.(ed.)
The Way of Synthesis
Phosphorus Ligands in
EvolutionofDesignandMethods
Asymmetric Catalysis
forNaturalProducts
SynthesisandApplications
2007
2008 Hardcover
Hardcover ISBN:978-3-527-32077-6
ISBN:978-3-527-31746-2
Hiersemann, M.,Nubbemeyer,U. (eds.)
Yamamoto, H.,Ishihara, K.(eds.)
The Claisen Rearrangement
Acid Catalysis in Modern
MethodsandApplications
Organic Synthesis
2007
2008 Hardcover
Hardcover ISBN:978-3-527-30825-5
ISBN:978-3-527-31724-0
Cornils,B.,Herrmann, W.A.,
Maruoka,K. (ed.) Muhler,M.,Wong,C.-H.(eds.)
Asymmetric Phase Transfer Catalysis from A to Z
Catalysis
AConciseEncyclopedia
2008 2007
Hardcover Hardcover
ISBN:978-3-527-31842-1 ISBN:978-3-527-31438-6
Cinchona Alkaloids in
Synthesis and Catalysis
Ligands, Immobilization and Organocatalysis
Edited by
Choong Eui Song
TheEditor AllbookspublishedbyWiley-VCHarecarefully
produced.Nevertheless,authors,editors,and
Prof.ChoongEuiSong publisherdonotwarranttheinformationcontained
SungkyunkwanUniversity inthesebooks,includingthisbook,tobefreeof
Dept.ofChemistry errors.Readersareadvisedtokeepinmindthat
Cheoncheon-dong300,Jangan-gu statements,data,illustrations,proceduraldetailsor
Suwon440-746 otheritemsmayinadvertentlybeinaccurate.
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To my wife Teresa

VII
Contents
Preface XV
Biography XVII
List of Contributors XIX
1 AnOverviewofCinchonaAlkaloidsinChemistry 1
ChoongEuiSong
1.1 BriefHistory 1
1.2 ActiveSitesinCinchonaAlkaloidsandTheirDerivatives 3
1.3 StructuralInformationonCinchonaAlkaloids 4
1.4 HowThisBookIsOrganized 8
References 9
PartOne CinchonaAlkaloidDerivativesasChiralityInducers
inMetal-CatalyzedReactions 11
2 CinchonaAlkaloidsasChiralityTransmittersinMetal-Catalyzed
AsymmetricReductions 13
Hans-UlrichBlaser
2.1 Introduction 13
2.2 HomogeneousSystemsforKetoneReductions 14
2.3 HeterogeneousPtandPdCatalystsModifiedwith
CinchonaAlkaloids 15
2.3.1 Background 15
2.3.2 Catalysts 16
2.3.3 ModifiersandSolvents 16
2.3.4 SubstrateScopeforPtCatalysts 17
2.3.4.1 a-KetoAcidDerivatives 17
2.3.4.2 a,g-DiketoEsters 18
2.3.4.3 FluorinatedKetones 18
2.3.4.4 a-KetoAcetals 20
2.3.4.5 a-KetoEthers 20
2.3.4.6 MiscellaneousKetones 21
VIII Contents
2.3.5 SubstrateScopeforPdCatalysts 21
2.4 IndustrialApplications 22
2.5 Conclusions 25
References 26
3 CinchonaAlkaloidsasChiralLigandsinAsymmetricOxidations 29
DavidJ.Ager
3.1 Introduction 29
3.2 AsymmetricDihydroxylationofAlkenes 30
3.2.1 EarlyReactions 30
3.2.2 BisalkaloidLigands 33
3.2.3 Mechanism 35
3.2.4 Variations 36
3.2.5 SubstratesandSelectivity 38
3.2.5.1 SimpleAlkenes 38
3.2.5.2 FunctionalizedAlkenes 38
3.2.5.3 Polyenes 43
3.2.5.3.1 NonconjugateOlefins 43
3.2.5.3.2 ConjugatedPolyenes 43
3.2.5.4 DoubleAsymmetricInduction 44
3.2.5.5 Resolutions 50
3.2.6 SomeReactionsof1,2-Diols 51
3.2.6.1 CyclicSulfatesandSulfites 54
3.3 Aminohydroxylation 56
3.4 SulfurOxidations 61
3.5 Summary 61
References 62
4 CinchonaAlkaloidsandtheirDerivativesasChiralityInducers
inMetal-PromotedEnantioselectiveCarbon–Carbonand
Carbon–HeteroatomBondFormingReactions 73
RavindraR.Deshmukh,DoHyunRyu,andChoongEuiSong
4.1 Introduction 73
4.2 NucleophilicAdditiontoCarbonylorImineCompounds 74
4.2.1 OrganozincAddition 74
4.2.1.1 DialkylzincAdditiontoAldehydes 74
4.2.1.2 DialkylzincAdditiontoImines 75
4.2.1.3 AdditionofAlkynylzincstoCarbonyls 77
4.2.2 AsymmetricReformatskyReaction 78
4.2.3 Indium-MediatedAddition 79
4.2.4 AsymmetricCyanation 81
4.2.4.1 CyanohydrinSynthesis 81
4.2.4.2 StreckerSynthesis 84
4.2.5 ReactionsofChiralAmmoniumKeteneEnolatesasNucleophiles
withDifferentElectrophiles 86