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Stereoselective Synthesis in Organic Chemistry

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Table of Contents

1 Stereochemical Principles.- 1.1 Introduction.- 1.2 Chirality.- 1.3 Diastereotopic Groups and Faces.- 1.4 Enantiotopic Groups and Faces.- 1.5 Homotopic Groups and Faces.- 1.6 Homochiral Relationships.- 1.7 Selectivity in Organic Synthesis.- 1.7.1 Chemoselectivity.- 1.7.2 Regioselectivity.- 1.7.3 Diastereoselectivity.- 1.7.4 Enantioselectivity.- Reactions in Presence of Chiral Additives.- Reactions Involving Covalent Linkages of Chiral Auxiliary Groups with Substrates.- Reactions with Chiral Reagents.- Reactions with Enzymes.- 1.8 References.- 2 Stereoselective Catalytic Reductions.- 2.1 Homogeneous Catalytic Hydrogenations.- 2.1.1 Hydrogenation of Olefins.- Hydrogenation with Rh-complexes.- Tetrasubstituted Olefins.- Substituted Itaconate Esters.- Hydrogenation with Ru-complexes.- Allylic and Homoallylic Alcohols.- Unsaturated Carboxylic Acids.- Dicarboxylic Acids.- Dehydroamino Acids.- Prochiral Ketones.- Hydrogenation with Ti-complexes.- Hydrogenation with Co-complexes.- Hydrogenation with Heterobimetallic Complexes.- 2.1.2 Catalytic Hydrosilylation.- Catalytic Hydrosilylation of Olefins.- Catalytic Hydrosilylation of Imines.- 2.1.3 Catalytic Hydrogenation of Ketones.- Direct Hydrogenation of Simple Ketones.- Direct Hydrogenation of Functionalized Ketones.- With Rhodium-Diphosphine Catalysts.- With Ruthenium Complexes.- With Copper Complexes.- Hydrogenation of Ketones via Derivatization.- Hydrogenation of Simple Ketones via Hydrosilylation.- Hydrogenation of Functionalized Ketones via Hydrosilylation.- Hydrogenation of Ketones via Enol Phosphinates.- 2.2 Heterogeneous Catalytic Hydrogenations.- 2.2.1 Enantioselective Heterogeneous Catalytic Hydrogenations.- 2.2.2 Diastereoselective Heterogeneous Catalytic Hydrogenations.- Asymmetric Hydrogenation of Carbon-Carbon Double Bonds.- Hydrogenation of N-Acyl-?,ss-Dehydroamino Acids.- Asymmetric Hydrogenation of Cyclic Dehydropeptides.- Asymmetric Hydrogenation of other Carbonyl Compounds.- Asymmetric Hydrogenation of Benzoylformic Acid Esters.- Asymmetric Hydrogenation of ?-Keto Amides.- Asymmetric Hydrogenation of Carbon-Nitrogen Double Bonds.- Hydrogenation of Imines, Oximes and Hydrazones.- 2.3 References.- 3 Stereoselective Non-Catalytic Reductions.- 3.1 Enantioselective Non-Catalytic Reductions.- 3.1.1 Chiral Metal-hydride Complexes.- Lithium Aluminium Hydride Modified with Chiral Groups.- LAH Modified with Alcohols.- LAH Modified with Amino Alcohols.- Chiral Boranes and Borohydrides.- Chiral Alkylboranes.- Chiral Borohydride Reagents.- NaBH4-derived Reagents.- Phase Transfer Catalyzed Reductions.- LiBH4 Reductions.- Super Hydrides.- 3.1.2 Chiral Metal Alkyls and Alkoxides.- 3.1.3 Chiral Dihydropyridine Reagents.- 3.2 Diastereoselective Non-Catalytic Reductions.- 3.2.1 Cyclic Substrates.- 3.2.2 Acyclic Substrates.- 1, 2- Induction.- 1,3-, 1,4- and 1,6- Inductions.- Cyclic Ketones.- 3.3 References.- 4 Stereoselective Carbon-Carbon Bond Forming Reactions.- 4.1 Nucleophilic Additions to Aldehydes and Ketones.- 4.1.1 Enantioselective Addition Reactions.- 4.1.2 Diastereoselective Addition Reactions.- Diastereoselective Additions to Carbonyl Compounds.- Diastereoselective Additions to Cyclic Ketones.- 4.1.3 Addition of Chiral Reagents.- 4.1.4 Stereoselectivity of Nucleophilic Addition Reactions.- 4.2 Asymmetric Catalytic Hydrocarbonylations.- 4.2.1 Asymmetric Hydroformylations.- Asymmetric Hydroformylation with Homogeneous Catalysts.- Asymmetric Hydroformylations with Heterogeneous Catalysts.- 4.2.2 Asymmetric Hydroesterification.- 4.3 Asymmetric Aldol Reactions.- 4.3.1 Stereochemistry of the Aldol Reaction.- Transition State Models in the Aldol Reaction.- 4.3.2 Addition of Enolates to Achiral Aldehydes.- Generation and Aldol Reactions of Enolates.- Li Enolates in Aldol Reactions.- Ketone Enolates.- Ester and Lactone Enolates.- Amide and Lactam Enolates.- Thioester and Thioamide Enolates.- Carboxylic Acid Dianions.- Boron Enolates in Aldol Reactions.- Magnesium Enolates in Aldol Reactions.- Titanium Enolates in Aldol Reactions.- Zinc Enolates in Aldol Reactions.- Tin Enolates in Aldol Reactions.- Silicon Enolates in Aldol Reactions.- Zirconium Enolates in Aldol Reactions.- 4.3.3 Addition of Chiral Enolates to Achiral Aldehydes and Unsymmetric Ketones (the Cross Aldol Reaction).- Metal Atoms as Chiral Centres in Aldol Reactions.- Chiral Ketone Enolates in Aldol Reactions.- Chiral Azaenolates in Aldol Reactions.- 4.3.4 Addition of Achiral Enolates to Chiral Aldehydes.- 4.3.5 Reactions of Chiral Aldehydes with Chiral Enolates.- 4.4 Allylmetal and Allylboron Additions.- 4.4.1 Configurational Stability of Allylmetal Compounds.- 4.4.2 Stereochemistry of Allylmetal Additions.- 4.4.3 Addition of Allylboron Compounds.- 4.4.4 Addition of Allyltitanium Compounds.- 4.4.5 Addition of Allylstannanes.- 4.4.6 Addition of Allylsilanes.- 4.4.7 Palladium-Catalyzed Asymmetric Allylation.- 4.4.8 Chromium (II)-Catalyzed Allylic Additions.- 4.4.9 Addition of other Allylmetals.- 4.5 Asymmetric Alkylation Reactions.- 4.5.1 Alkylation of Chiral Enolates.- Exocyclic Enolates.- Endocyclic Enolates.- Norbornyl Enolates.- 4.5.2 Alkylation of Imine and Enamine Salts.- 4.5.3 Alkylation of Chiral Hydrazones.- 4.5.4 Alkylation of Chiral Oxazolines.- Synthesis of Alkyl Alkanoic Acids.- Synthesis of ?-Hydroxyacids.- Synthesis of Butyrolactones and Valerolactones.- Synthesis of ss-Alkylalkanoic Acid.- Synthesis of Unsubstituted 1,4-Dihydropyridines.- Synthesis of Resin-Bound Oxazolines.- Alkylation via Diketopiperazines.- 4.5.5 Alkylation of Sulfoxides and Dithianes.- 4.5.6 Michael Addition Reactions.- Addition of Chiral Anions.- Addition of Achiral Anions Complexed with Chiral Ligands to Prochiral Michael Acceptors.- Addition of Achiral Anions to Michael Acceptors Having One or More Chiral Centres.- Addition with Optically Active Transition Metal-Ligand Catalysts.- 4.6 Pericyclic Reactions.- 4.6.1 Asymmetric Cycloaddition Reactions.- Asymmetric Diels-Alder Reactions.- Addition to Chiral Dienophiles.- Addition to Chiral Dienes.- Chiral Catalysts.- 4.6.2 Asymmetric [2+2] Cycloadditions.- 4.6.3 Asymmetric 1,3-Dipolar [3+2] Cycloadditions.- 4.6.4 Sigmatropic Rearrangements.- [3, 3] Sigmatropic Rearrangements.- [2, 3] Sigmatropic (Wittig) Rearrangements.- Allylsulfenate Rearrangements.- 4.6.5 Ene Reactions.- Intermolecular Ene Reactions.- Intramolecular Ene Reactions.- 4.7 References.- 5 Asymmetric Oxidations.- 5.1 Asymmetric Epoxidation.- 5.1.1 Asymmetric Epoxidation of Allylic Alcohols.- Katsuki-Sharpless Epoxidation.- 5.1.2 Asymmetric Epoxidation of other Substrates.- 5.2 Asymmetric Oxidation of Sulfides.- 5.3 Asymmetric Oxidation of Selenides.- 5.4 Asymmetric Hydroxylations.- 5.4.1 Vicinal Hydroxylations.- 5.5 Asymmetric Oxidation of Aromatic Substrates via Donor-Acceptor Interaction.- 5.6 References.- 6 Asymmetric Carbon-Heteroatom Bond Formations.- 6.1 Carbon-Oxygen Bond Formation.- 6.1.1 Asymmetric Halolactonization.- 6.1.2 Asymmetric Hydroboration.- 6.2 Carbon-Nitrogen Bond Formation.- 6.2.1 Halocyclization.- Iodolactamization.- 6.2.2 Mercuricyclization.- 6.3 Carbon-Sulfur Bond Formation.- 6.4 Carbon-Phosphorus Bond Formation.- 6.5 Stereoselective C-H Bond Formation and Proton Migration.- 6.6 References.- 7 Enzyme-Catalyzed Reactions.- 7.1 Enzyme Specificity.- 7.1.1 Enantiomeric Specificity of Enzymes.- 7.1.2 Prochiral Stereospecificity.- Additions to Stereoheterotopic Faces.- Stereoheterotopic Groups and Atoms.- 7.2 Meso Compound Transformations.- 7.3 Multienzyme Systems.- 7.4 References.- 8 Stereoselective Free Radical Reactions.- 8.1 Free Radical Chain Reactions.- 8.1.1 The Tin Hydride Method.- Intramolecular Radical Cyclizations.- Intermolecular Radical Additions.- 8.1.2 The Mercury Hydride Method.- Intramolecular Cyclization Reactions.- Intermolecular Radical Reactions.- Cyclic Radicals.- Acyclic Substrates.- 8.1.3 The Fragmentation Method.- 8.1.4 The Barton (Thiohydroxamate Ester) Method.- 8.1.5 The Atom Transfer Method.- Hydrogen Atom Transfer Addition and Cyclization.- Halogen Atom Transfer.- Halogen Atom Transfer Additions.- Halogen Atom Transfer Cyclizations.- Halogen Atom Transfer Annulations.- 8.1.6 Heteroatom-Halogen Donors.- 8.1.7 Organocobalt Transfer Method.- 8.2 Non-Chain Radical Reactions.- 8.3 References.- 9 Miscellaneous Stereoselective Reactions.- 9.1 Asymmetric Cyclopropanations.- 9.2 References.

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