Chapter
Chapter 2 Asymmetric Dearomatization with Chiral Auxiliaries and Reagents
2.2 Chiral 𝛔-Bound Auxiliaries
2.2.2 Imines, Oxazolidines, and Hydrazones
2.2.3 Chiral Ethers and Amines
2.3 Diastereospecific Anionic Cyclizations
2.4 Use of Chiral Reagents
2.4.1 Chiral Bases in Dearomatizing Cyclizations
2.4.2 Chiral Nucleophiles
2.4.3 Chiral Ligands in Enantioselective Nucleophilic Additions
2.5.1 Planar Chiral 𝛈6-Arene Complexes
2.5.2 𝛈6-Arene Complexes with a Chiral Ligand
2.5.3 Complexes with Stereogenic Metal Centers
Chapter 3 Organocatalytic Asymmetric Transfer Hydrogenation of (Hetero)Arenes
3.2 Organocatalytic Asymmetric Transfer Hydrogenation of Heteroaromatics
3.2.1.2 2-Substituted Quinolines
3.2.1.3 4-Substituted Quinolines
3.2.1.4 3-Substituted Quinolines
3.2.1.5 2,3-Disubstituted Quinolines
3.2.1.6 Spiro-Tetrahydroquinolines
3.2.2 Benzoxazines, Benzothiazines, and Benzoxazinones
3.2.3 Benzodiazepines and Benzodiazepinones
3.2.6 Quinoxalines and Quinoxalinones
3.3 Organocatalytic Asymmetric Transfer Hydrogenation in Aqueous Solution
3.4.2 In situ Generation of the Heteroarene
3.4.3 Dearomatization of Pyridine/Asymmetric aza-Friedel-Crafts Alkylation Cascade
3.4.4 Combining Photochemistry and Brønsted Acid Catalysis
3.5 Cooperative and Relay Catalysis: Combining Brønsted Acid- and Metal-Catalysis
3.5.2 Improvements in Transfer Hydrogenation
3.5.2.1 Regenerable Hydrogen Sources
3.5.2.2 Asymmetric Relay Catalysis (ARC)
3.5.3 Cooperative Metal-Brønsted Acid Catalysis
3.6 Summary and Conclusion
Chapter 4 Transition-Metal-Catalyzed Asymmetric Hydrogenation of Aromatics
4.2 Catalytic Asymmetric Hydrogenation of Five-Membered Heteroarenes
4.2.1 Catalytic Asymmetric Hydrogenation of Azoles and Indoles
4.2.1.1 Rhodium-Catalyzed Asymmetric Hydrogenation of Indoles
4.2.1.2 Ruthenium-Catalyzed Asymmetric Hydrogenation of Azoles
4.2.1.3 Palladium-Catalyzed Asymmetric Hydrogenation of Azoles
4.2.1.4 Iridium-Catalyzed Asymmetric Hydrogenation of Indoles
4.2.2 Catalytic Asymmetric Hydrogenation of Oxygen-Containing Heteroarenes
4.2.3 Catalytic Asymmetric Hydrogenation of Sulfur-Containing Heteroarenes
4.3 Catalytic Asymmetric Hydrogenation of Six-Membered Heteroarenes
4.3.1 Catalytic Asymmetric Hydrogenation of Azines
4.3.1.1 Iridium-Catalyzed Asymmetric Hydrogenation of Pyridines
4.3.1.2 Iridium-Catalyzed Asymmetric Hydrogenation of Pyrimidines
4.3.2 Catalytic Asymmetric Hydrogenation of Benzo-Fused Azines
4.3.2.1 Iridium-Catalyzed Asymmetric Hydrogenation of Quinolines
4.3.2.2 Ruthenium-Catalyzed Asymmetric Hydrogenation of Quinolines
4.3.2.3 Iridium-Catalyzed Asymmetric Hydrogenation of Isoquinolines
4.3.2.4 Iridium-Catalyzed Asymmetric Hydrogenation of Quinoxalines
4.3.2.5 Ruthenium-Catalyzed Asymmetric Hydrogenation of Quinoxalines
4.3.2.6 Iron-Catalyzed Asymmetric Hydrogenation of Quinoxalines
4.3.2.7 Catalytic Asymmetric Hydrogenation of Miscellaneous Six-Membered Heteroarenes
4.3.3 Catalytic Asymmetric Reduction of Quinolines with Reducing Agents Other Than H2
4.4 Catalytic Asymmetric Hydrogenation of Carbocyclic Arenes
4.4.1 Ruthenium-Catalyzed Asymmetric Hydrogenation of Carbocycles in Benzo-Fused Heteroarenes
4.4.2 Ruthenium-Catalyzed Asymmetric Hydrogenation of Naphthalenes
4.5 Summary and Conclusion
Chapter 5 Stepwise Asymmetric Dearomatization of Phenols
5.2 Stepwise Asymmetric Dearomatization of Phenols
5.2.1 Asymmetric [4+2] Reaction
5.2.2 Asymmetric Heck Reaction
5.2.3 Asymmetric (Hetero) Michael Reaction
5.2.4 Asymmetric Stetter Reaction
5.2.5 Asymmetric Rauhut-Currier Reaction
5.2.6 Asymmetric 1,6-Dienyne Cyclized Reaction
5.3 Conclusion and Perspective
Chapter 6 Asymmetric Oxidative Dearomatization Reaction
6.2 Diastereoselective Oxidative Dearomatization using Chiral Auxiliaries
6.3 Enantioselective Oxidative Dearomatization using Chiral Reagents or Catalysts
6.3.1 Chiral Transition Metal Complexes
6.3.2 Chiral Hypervalent Iodines(III, V) and Hypoiodites(I)
6.4 Conclusions and Perspectives
Chapter 7 Asymmetric Dearomatization via Cycloaddition Reaction
7.2 [2 + 1] Cycloaddition
7.2.1 Asymmetric Büchner Reaction
7.2.2 Cyclopropanation of Heterocyclic Compounds
7.3 [3 + 2] Cycloaddition
7.4 [3 + 3] Cycloaddition
7.5 [4 + 2] Cycloaddition
7.6 [4 + 3] Cycloaddition
Chapter 8 Organocatalytic Asymmetric Dearomatization Reactions
8.3 Oxidative Dearomatization
8.6 Nucleophilic Dearomatization
8.7 Summary and Conclusion
Chapter 9 Dearomatization via Transition-Metal-Catalyzed Allylic Substitution Reactions
9.2 Dearomatization of Indoles and Pyrroles via Transition-Metal-Catalyzed Allylic Substitution Reactions
9.3 Dearomatization of Phenols via Transition-Metal-Catalyzed Allylic Substitution Reactions
9.4 Dearomatization of Phenols and Indoles via Activation of Propargyl Carbonates with Pd Catalyst
Chapter 10 Dearomatization via Transition-Metal-Catalyzed Cross-Coupling Reactions
10.1 Introduction: From Cross-Coupling to Catalytic Dearomatization
10.2 Dearomatization of Phenolic Substrates
10.3 Dearomatization of Nitrogen-Containing Substrates
10.4 Conclusion and Outlook
Chapter 11 Dearomatization Reactions of Electron-Deficient Aromatic Rings
11.2 Dearomatization of Activated Pyridines and Other Electron-Deficient Heterocycles
11.2.1 Dearomatization via Alkyl Pyridinium Salts
11.2.1.1 Reduction with Borohydrides
11.2.1.2 Reduction with Na2S2O4
11.2.1.3 Reduction with Other Reducing Agents
11.2.1.4 Nucleophilic Addition of Grignard Reagents
11.2.1.5 Nucleophilic Addition of Cyanide
11.2.1.6 Addition of Other Carbon Nucleophiles
11.2.2 Dearomatization via Alkoxycarbonylpyridinium Salts
11.2.2.1 Reduction with Hydride Nucleophiles
11.2.2.2 Addition of Metal Nucleophiles, Including Grignard Reagents
11.2.2.3 Addition of Enolates and Related Carbon Nucleophiles
11.2.2.4 Nucleophilic Addition of Cyanide
11.2.2.5 Addition of Other Nucleophiles
11.2.3 Dearomatization via Acyl Pyridinium Salts
11.2.3.1 Reduction with Hydride Reducing Agents
11.2.3.2 Addition of Metal Nucleophiles Including Grignard Reagents
11.2.3.3 Addition of Enolates and Related Carbon Nucleophiles
11.2.4 Dearomatization through Other Pyridinium Cations
11.3 Summary and Conclusion
Chapter 12 Asymmetric Dearomatization Under Enzymatic Conditions
12.2 Dearomatizing Arene cis-Dihydroxylation
12.2.2 Types of Arene Dioxygenase
12.2.3 Substrate Scope and Regioselectivity
12.2.3.1 Monocyclic Substituted Benzene Substrates (Excluding Biaryls)
12.2.3.2 Biaryl Substrates
12.2.3.3 Naphthalene Substrates
12.2.3.4 Benzoic Acid Substrates
12.2.3.5 Heterocyclic Substrates (Mono- and Bicyclic)
12.2.3.6 Bicyclic Carbocyclic Substrates (Other than Naphthalenes)
12.2.3.7 Tricyclic Substrates (Carbo- and Heterocyclic)
12.2.4 Availability of Arene cis-Diols
12.2.5.2 Pharmaceuticals and Agrochemicals
12.2.5.4 Flavors and Fragrances
12.2.5.6 Ligands and MOFs
12.2.6 Increasing the Substrate Scope
12.2.7 Accessing Both Enantiomeric Series
12.2.8 Improvements to the Production Process
12.3 Dearomatizing Arene Epoxidation
12.4 Dearomatizing Arene Reduction
12.5 Summary and Conclusion
Chapter 13 Total Synthesis of Complex Natural Products via Dearomatization
13.2 Natural Products Synthesis via Oxidative Dearomatization
13.2.1 Enzymatic Dihydroxylative Dearomatization of Arene
13.2.2 Oxidative Dearomatization of Phenol
13.2.3 Oxidative Cycloisomerization Reaction of Phenol
13.2.4 Oxidative Dearomatization of Indole in Synthesis of Natural Products
13.3 Dearomatization via Cycloaddition in Synthesis of Natural Products
13.4 Dearomatization via Nucleophilic Addition in Synthesis of Natural Products
13.5 Reductive Dearomatization in Synthesis of Natural Products
13.6 Dearomatization via Electrophilic Addition in Synthesis of Natural Products
13.7 Dearomatization via Intramolecular Arylation in Natural Products Synthesis
13.8 Summary and Perspective
Chapter 14 Miscellaneous Asymmetric Dearomatization Reactions
14.2 Miscellaneous Asymmetric Dearomatization Reactions
14.3 Conclusions and Perspectives
Asymmetric Dearomatization Reactions
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