Chapter
Volume 1: Privileged Catalysts
Part I: Amino Acid-Derived Catalysts
1: Proline-Related Secondary Amine Catalysts and Applications
1.2 Prolinamide and Related Catalysts
1.3 Prolinamine and Related Catalysts
1.4 Proline Tetrazole and Related Catalysts
1.5 Prolinamine Sulfonamide and Related Catalysts
1.6 Prolinamine Thiourea and Related Catalysts
2: TMS-Prolinol Catalyst in Organocatalysis
2.3 Iminium-Ion Activation
2.6 Trienamine Activation
2.7 Summary and Conclusions
3: Non-Proline Amino Acid Catalysts
3.2 Primary Amino Acids in Amino Catalysis
3.3 Primary Amino Acid-Derived Organic Catalysts
3.3.1 Unmodified Amino Acids
3.3.2 Protected Primary Amino Acids
3.3.3 Primary Amino Acid-Derived Diamine Catalysts
3.3.4 Other Primary Amino Acid Catalysts
3.4 Applications of Non-Proline Primary Amino Acid Catalysts
4: Chiral Imidazolidinone (MacMillan’s) Catalyst
4.4 Cascade Reaction – Merging Iminium and Enamine Catalysis
5: Oligopeptides as Modular Organocatalytic Scaffolds
5.2 C–C Bond Forming Reactions
5.2.3 Morita–Baylis–Hillman Reactions
5.2.4 Hydrocyanation of Aldehydes
5.3 Asymmetric Acylations
5.4 Asymmetric Phosphorylations
5.5 Enantioselective Oxidations
5.7 Summary and Conclusions
Part II: Non-Amino Acid-Derived Catalysts
6: Cinchonas and Cupreidines
6.2 Cinchona Alkaloid Derivatives
6.3 Natural Cinchona Alkaloids, Cupreine, and Cupreidine
6.3.1 Structural Properties
6.3.2 Catalysis with Natural Cinchona Alkaloids
6.3.3 Catalysis with Cupreine and Cupreidine
6.4 Cinchona Alkaloids with an Ether or Ester Group at C9
6.4.1 Structural Properties
6.4.2 Catalysis with C9 Ethers of Natural Cinchona Alkaloids
6.4.3 Catalysis with C9 Ethers of Cupreine and Cupreidine
6.4.4 Catalysis with C9 Esters
6.5 Cinchona Alkaloid Derivatives with a Sulfonamide, Urea, Thiourea, Squaramide, or Guanidine Function
6.5.1 Structural Properties
6.5.2 Catalysis with C9 and C6′ Thiourea Derivatives
6.5.3 Catalysis with C9 Sulfonamide, Squaramide, and Guanidine Derivatives
6.6 Cinchona Alkaloids with a Primary Amine Group at C9
6.6.1 Structural Properties
6.6.2 Catalysis with C9 Amino Derivatives
6.7 Cinchona Alkaloids in Phase-Transfer Catalysis
6.9 Some Novel Cinchona Alkaloid Derivatives
7.2 Chiral Lewis Base Catalysts
7.2.2 Bipyridine N,N′-Dioxides
7.2.3 Bisphosphine Dioxides
7.4 Chiral C2-Symmetric Secondary and Primary Amines
7.5 Chiral C2-Symmetric Brønsted Bases: Guanidines
7.6 Chiral C2-Symmetric Brønsted Acids
7.6.1 Binaphthol and Biphenol Derivatives
7.6.2 Pyridinium Disulfonates
7.6.4 Chiral Disulfonimides
7.7 Chiral C2-Symmetric Bis-Thioureas
7.8 Chiral C2-Symmetric Aminophosphonium Ions
7.9 Summary and Conclusions
8: Planar Chiral Catalysts
8.2.4 N-Heterocyclic Carbenes
8.5 Summary and Conclusions
9: Dynamic Approaches towards Catalyst Discovery
9.2.1 Self-Assembled Organocatalysts
9.2.2 Catalysis in Confined Self-Assembled Space
9.3 Self-Selected Catalysts
9.3.1 Dynamic Combinatorial Chemistry
Proline Derivatives and Proline Analogs
b) Proline Tetrazole Catalysts and Analogs
e) Diarylprolinol Derivatives
g) Phosphorus Derivatives
h) Thioethers and Acetals
k) Piperazine Derivatives
l) Ionic Liquid Tagged Proline Derivatives
m) Polymer-Supported Prolines/Pyrrolidines
n) Polymer-Supported Prolinamides
o) Polymer-Supported Diarylprolinols
p) Silica-Supported Derivatives
a) Unmodified α-Amino Acids
c) N-Aryl Valinamide Derivatives
Chiral Imidazolidinones (MacMillan’s Catalysts and Analogs)
a) “First-Generation” Imidazolidinone Catalysts
b) Supported “First-Generation” Imidazolidinone Catalysts
c) “Second-Generation” Imidazolidinone Catalysts
Di- and Oligopeptide Catalysts
a) Proline-Containing Di- and Oligopeptides
c) Non-Proline Oligopeptides
a) Cinchonidine, Quinine, Cupreine, Quinidine, Cinchonine and Cupreidine Derivatives
b) 9-Aza-Cinchona Derivatives
c) Biphenyl/Bipyridyl Catalysts
a) α-Amino Acid-Derived Diamines
b) 1,2-Diaminocyclohexane Derivatives
c) Diphenylethylenediamine Derived Catalysts
d) Miscellaneous Diamines
Carbohydrate-Derived Catalysts
Terpene-Derived Catalysts
Part I: Asymmetric Catalysis with Non-Covalent Interactions
10.2 Chiral Alcohol Catalysts
10.3 Chiral Squaramides as Hydrogen-Bond Donor Catalysts
10.3.2 Summary and Outlook
10.4 Guanidines/Guanidiniums
10.5 Miscellaneous Brønsted Acids
10.5.2 Tetraaminophosphoniums
10.5.3 Axially Chiral Dicarboxylic Acids
10.5.4 Stronger Brønsted Acids
11: Brønsted Acids: Chiral Phosphoric Acid Catalysts in Asymmetric Synthesis
11.1.1 Design of Chiral Phosphoric Acids
11.2 Reaction with Imines
11.2.2 Hydrophosphonylation
11.2.3 Cycloaddition Reaction
11.2.4 Transfer Hydrogenation
11.3 Friedel–Crafts Reaction
11.4 Intramolecular Aldol Reaction
11.5 Ring Opening of meso-Aziridines
12: Brønsted Acids: Chiral (Thio)urea Derivatives
12.1.1 Explicit Double Hydrogen-Bonding Interactions
12.1.2 The Beginnings of (Thio)urea Catalysis
12.2 Important Chiral (Thio)urea Organocatalysts
12.2.1 Takemoto’s Catalyst
12.2.2 Cinchona Alkaloids in (Thio)urea Organocatalysis
12.2.3 Pyrrolidine-(thio)urea Catalysis
12.2.4 Nagasawa’s Catalyst
12.2.5 Ricci’s Thiourea Catalyst
12.2.6 Binaphthylamine Scaffolds in (Thio)urea Catalysis
12.2.7 Jacobsen’s Catalyst Family
12.2.8 N-Sulfinyl (Thio)urea Catalysts
13.2.1 Cinchona Alkaloids in Asymmetric Transformations
13.2.2 Asymmetric Activation of Conjugate Addition to Enones
13.2.3 Asymmetric Activation of Conjugate Addition to Imines
13.2.4 Asymmetric Aminations
13.2.5 Asymmetric Activation of Isocyanoacetates
13.2.6 Asymmetric Diels–Alder Reaction
13.3 Brønsted Base-Derived Thiourea Catalysts
13.3.1 Asymmetric Conjugate Addition with Carbonyls and Imines
13.3.2 Asymmetric Conjugate Additions with Non-Traditional Substrates
13.4 Chiral Guanidine Catalysts
13.4.1 Asymmetric Conjugate Addition to Enones and Imines
13.4.2 Asymmetric Diels–Alder Reactions
14: Chiral Onium Salts (Phase-Transfer Reactions)
14.2 Phase-Transfer Catalysis
14.2.1 Phase-Transfer Reaction of Active Methylene or Methine Compounds with Inorganic Base
14.2.2 Phase-Transfer Catalyzed Addition of Anion Supplied as Metal Salt
14.2.3 Base-Free Neutral Phase-Transfer Reaction
14.4 Onium Phenoxides and Related Compounds
14.4.1 Onium Phenoxides as Lewis Base Catalysts
14.4.2 Onium Phenoxides and Related Compounds as Brønsted Base Catalysts
15.2 Allylation Reactions
15.2.1 Catalytic Allylation of Aldehydes
Reaction of Allyltrichlorosilane (2a) with Benzaldehyde (1a)
15.2.2 Stoichiometric Allylation of Aldehydes and Ketones
Allylation of Imines and Hydrazones
15.3 Propargylation, Allenylation, and Addition of Acetylenes
15.3.1 Addition to Aldehydes
15.3.2 Addition to Imines
15.4 Aldol-Type Reactions
Trichloro[(1-phenylethenyl)oxy]silane (76e)
(S)-(−)-4-Hydroxy-4-phenyl-2-butanone [(S)-(−)-(78e)]
(S)-(-)-Methyl 3-Hydroxy-3-phenylbutanoate (89, R1 = Ph, R2 = Me)
Methyl (R)-3-Hydroxy-3-phenylpropanoate (R)-(+)-93a (R1 = Ph, R2 = H, R3 = Me)
15.5 Cyanation and Isonitrile Addition
15.5.1 Cyanation of Aldehydes
Catalytic Asymmetric Cyanation with (R)-BINOLi/-PrOLi (10 mol%)
N-tert-Butyl-2-hydroxy-2-(2-naphthyl)acetamide (S)-(+)-(101)
15.5.2 Cyanation of Imines (Strecker Reaction)
Typical Procedure for the Catalytic Hydrosilylation of Imines
Typical Procedure for the Catalytic Desymmetrization of meso-Epoxides
15.8 Conclusion and Outlook
16.2 Silyl Cation Based Catalysts
16.3 Hypervalent Silicon Based Catalysts
16.4 Phosphonium Cation Based Catalysts
16.5 Carbocation Based Catalysts
16.7 Miscellaneous Catalysts
Part II: Asymmetric Catalysis with Covalent Interactions
17: Rationalizing Reactivity and Selectivity in Aminocatalytic Reactions
17.2 Secondary Amine Catalysis
17.2.1 Mechanism of Secondary Amine Catalysis
17.3 Stereoselectivity in Proline-Catalyzed Reactions
17.3.1 Transition State Models for Proline-Catalyzed Reactions
17.3.2 Limitations of Hydrogen-Bonding Guided Transition State Models
17.4 Mechanism and Stereoselectivity in Organocatalytic Cascade Reactions
17.4.1 Stereoselectivity in Other Amino Acid Catalyzed Reactions
17.5 Rational Design of Catalysts
17.6 Summary and Conclusions
18.2 Reactions of Acyl Anion Equivalents
18.2.3 Hydroacylation Reactions
18.3.1 Reactions of α-Reducible Aldehydes
18.3.2 Reactions of Enals and Ynals
18.4 Umpolung of Activated Olefins
18.5 Nucleophilic Catalysis
19.1.1 Ketone-Mediated Epoxidation
19.1.2 Iminium Salt-Catalyzed Epoxidation
19.1.3 Aspartate-Derived Peracid Catalysis
19.2 Hypervalent Iodine-Catalyzed Oxidations
19.2.1 Asymmetrical Naphthol Dearomatization
19.2.2 Enantioselective α-Oxysulfonylation of Ketones
19.3 Oxidation of Thioethers and Disulfides
19.4 Resolution of Alcohols by Oxidation
20.2 Enantioselective Sulfur Ylide Catalysis
20.3 Enantioselective Phosphorus and Arsenic Ylide Catalysis
20.4 Enantioselective Nitrogen Ylide Catalysis
20.5 Enantioselective Selenium and Tellurium Ylide Catalysis
20.6 Summary and Conclusions
Part III: Tuning Catalyst Activity and Selectivity by the Reaction Medium and Conditions
21: “Non-Classical” Activation of Organocatalytic Reactions (Pressure, Microwave Irradiation.)
21.2 Asymmetric Organocatalysis under High-Pressure Conditions
21.3 Asymmetric Organocatalysis under Microwave Irradiation – Thermal Effect
21.4 Asymmetric Organocatalysis under Ultrasound Irradiation
21.5 Asymmetric Organocatalysis under Ball Milling Conditions
21.6 Summary and Conclusions
22: Ionic Liquid Organocatalysts
22.2 Ionic Liquids as Recyclable Solvents for Asymmetric Organocatalytic Reactions
22.2.1 α-Amino Acid-Promoted Reactions in IL Media
22.2.2 Reactions in the Presence of Other Chiral Organocatalysts in IL Media
22.3 “Non-Solvent” Applications of Ionic Liquids and Their Congeners in Asymmetric Organocatalysis
22.3.1 Immobilization of Organocatalysts through Electrostatic Interaction with Ionic Fragments
22.3.2 Modification of Organocatalysts by Ionic Groups through Covalent Bonding
23: Polymer and Mesoporous Material Supported Organocatalysts
23.2 Polymer-Supported Organocatalysts
23.2.1 Polymer Resins for Immobilization of Chiral Organocatalysts
23.2.2 Polymer-Supported Cinchona Derivatives
23.2.3 Polymer-Supported Enamine–Iminium Organocatalysts
23.2.4 Miscellaneous Polymer-Supported Chiral Organocatalysts
23.3 Mesoporous-Supported Organocatalysts
23.3.1 Mesoporous Materials for Immobilization of Chiral Organocatalysts
23.3.2 Inorganic and Inorganic–Organic Hybrid Material Supported Chiral Organocatalysts
23.4 Conclusions and Outlook
24: Water in Organocatalytic Reactions
24.2.3 Prolines Substituted at the 4-Position
24.2.5 Supported Proline and Proline Derivatives
24.5 Diels–Alder Reaction
24.6 Miscellaneous Examples
Volume 3: Reactions and Applications
Part I: Alpha-Alkylation and Heteroatom Functionalization
25: SN2-Type Alpha-Alkylation and Allylation Reactions
25.1 SN2-Type Alkylation under Homogenous Conditions
25.2 Domino Reactions Including SN2-Type Alkylations
25.2.1 Michael/SN2 Reactions with the Halide on the Donor
25.2.2 Michael/SN2 Reactions with the Halide on the Acceptor
25.3 Intermolecular SN2′ Alkylations under Homogenous Conditions
26: Alpha-Alkylation by SN1-Type Reactions
26.2 SN1-Type Nucleophilic Reaction by Generation of Carbocations
26.3 Organocatalytic Stereoselective SN1-Type Reactions with Enamine Catalysis
26.4 Asymmetric SN1-Type α-Alkylation of Ketones
26.5 Combination of Enamine Catalysis and Lewis Acids in SN1-Type Reactions
26.6 Organocatalytic SN1-Type Reactions with Brønsted Acids
26.6.1 Organocatalytic SN1-Type Reactions with Brønsted Acids and Metals
26.7 SN1-Type Reaction Promoted by Chiral Thioureas
26.8 SN1-Type Organocatalytic Reaction of Iminium, Oxonium, and Aziridinium Intermediates
26.9 Conclusions and Perspectives
27: Alpha-Heteroatom Functionalization of Carbonyl Compounds
27.2 Enantioselective α-Pnictogenation of Carbonyl Compounds
27.2.1 Amination of Carbonyl Compounds
27.2.2 Phosphination of Carbonyl Compounds
27.3 Enantioselective α-Chalcogenation
27.3.2 Sulfenylation and Selenenylation Processes
27.4 Enantioselective α-Halogenation of Carbonyl Compounds
27.5 Summary and Conclusions
Part II: Nucleophile Addition to C=X Bonds
28: Aldol and Mannich-Type Reactions
28.2.1 Aldol Reactions in Enamine Catalysis
28.2.2 Mannich Reactions in Enamine Catalysis
28.3 Brønsted Acid Catalysis Including Hydrogen-Bond Catalysis
28.3.1 Aldol Reactions in Brønsted Acid and Hydrogen-Bond Catalysis
28.3.2 Mannich Reactions with Brønsted Acid and Hydrogen-Bond Catalysis
28.4 Brønsted Base Catalysis Including Bifunctional Catalysis
28.4.1 Aldol Reactions in Brønsted Base Catalysis Including Bifunctional Catalysis
28.4.2 Mannich Reactions in Brønsted Base Catalysis Including Bifunctional Catalysis
28.5 Phase-Transfer Catalysis
28.5.1 Aldol Reactions in Phase-Transfer Catalysis
28.5.2 Mannich Reactions in Phase-Transfer Catalysis
28.5.3 Quaternary Ammonium Salt-Catalyzed 6π Electrocyclization
28.6 N-Heterocyclic Carbene (NHC) Catalysis
28.6.1 NHC-Catalyzed Mannich-Type Reactions
28.7 Supported Organocatalysis
28.7.1 Covalently Supported Organocatalysts
28.7.2 Non-Covalently Supported Organocatalysts
28.7.3 Supported Organocatalysts in Multiphasic Systems
28.8 Summary and Conclusions
29: Additions of Nitroalkyls and Sulfones to C=X
29.1 Organocatalytic Addition of Nitroalkanes to C=O (The Henry Reaction)
29.1.1 Organocatalytic Addition of Nitroalkanes to Aldehydes
29.1.2 Organocatalytic Addition of Nitroalkanes to Ketones
29.2 Addition of Nitroalkanes to C=NR (The Aza-Henry or Nitro-Mannich Reaction)
29.2.1 Brønsted Base Catalyzed Aza-Henry Reactions
29.2.2 Hydrogen Bond Catalyzed Aza-Henry Reactions
29.2.3 Phase-Transfer Conditions (PTC)
29.3 Organocatalytic Addition of Sulfones to C=X
29.3.2 Organocatalytic Addition of Sulfones to C=O
29.3.3 Organocatalytic Addition of Sulfones to C=N
30: Hydrocyanation and Strecker Reactions
30.2 Amino-Acid Containing Catalysts for Carbonyl Hydrocyanation
30.3 Thiourea Catalysts for Carbonyl Hydrocyanation
30.4 C2-Symmetrical Guanidines and N,N′-Dioxides
30.5 Diketopiperazines as Catalysts for the Strecker Reaction
30.6 (Thio)urea Catalysts for the Strecker Reaction
30.7 Guanidines as Catalysts for the Strecker Reaction
30.8 N,N′-Dioxides and Bis-Formamides as Catalysts for the Strecker Reaction
30.9 Chiral Quaternary Ammonium Salts as Catalysts for the Strecker Reaction
30.10 BINOL-Phosphates as Catalysts for the Strecker Reaction
30.11 Other Catalysts for the Strecker Reaction
31: The Morita–Baylis–Hillman (MBH) and Hetero-MBH Reactions
31.2 Recent Mechanistic Insights into the MBH/aza-MBH Reaction and Its Asymmetric Version
31.2.1 Amine Catalyzed Mechanism
31.2.2 Phosphine Catalyzed Mechanism
31.2.3 Mechanistic Insights into the MBH/aza-MBH Reaction Using Co-catalytic Systems or Multi-/Bifunctional Catalysts
31.2.4 Stereoselectivity of the MBH/aza-MBH Reaction
31.3 Recent Developments of Essential Components
31.4 Recent Developments of Asymmetric MBH/aza-MBH Reactions
31.4.1 Asymmetric Induction with Substrates
31.4.2 Catalytic Asymmetric Induction with Chiral Lewis Bases
31.4.3 Catalytic Asymmetric Induction with Chiral Lewis Acids
31.4.4 Catalytic Asymmetric Induction with Chiral Brønsted Acids
32: Reduction of C=O and C=N
32.2 Hantzsch Ester as the Hydride Source
32.2.1 Reduction of C=N Bonds in Acyclic Systems
32.2.2 Reduction of C=N Bonds in Cyclic Substrates
32.2.3 Transfer Hydrogenation Combined with Other Transformations
32.2.4 Immobilized Chiral Catalysts for C=N Bond Reduction
32.2.5 Mechanistic Consideration
32.3 Trichlorosilane as the Reducing Reagent
32.3.1 Asymmetric Reduction of Ketimines
32.3.2 Reduction of Enamines
32.3.3 Reduction of C=N Bonds Catalyzed by Recoverable Lewis Base Catalysts
32.3.4 Asymmetric Reduction of C=O Bonds
32.4 Other Hydrogen Sources
32.4.3 Hydrogen as the Source?
32.5 Summary and Conclusions
Part III: Nucleophile Addition to C=C Bonds
33: Addition to α,β-Unsaturated Aldehydes and Ketones
33.1.1 Iminium Activation
33.2 Nucleophilic Addition to Enals and Ketones
33.2.1 Iminium Activation
33.2.2 Scope of the Nucleophilic Addition to Enals
33.2.3 Scope of the Nucleophilic Addition to α,β-Unsaturated Ketones
34: Addition to Nitroolefins and Vinyl Sulfones
34.2 Addition to Nitroolefins
34.2.1 Enamine Activation
34.2.2 Hydrogen Bonding Activation
34.2.5 Challenging Substrates
34.3 Addition to Vinyl Sulfones
34.3.1 Enamine Activation of Aldehydes and Ketones
34.3.2 Non-Covalent Activation
34.4 Addition to Vinyl Selenones
34.5 Summary and Conclusions
35: Organocatalyzed Asymmetric Arylation and Heteroarylation Reactions
35.2 Representative Classes of Electrophiles
35.2.1 α,β-Unsaturated Aldehydes
35.2.2 α,β-Unsaturated Enones
35.2.4 Carbonyl Compounds
35.2.5 Imines (Aza-Friedel–Crafts Reaction)
35.2.6 Other Electrophiles
35.3 Friedel–Crafts in Organocascade Transformations
35.4 Application in Biologically Interesting and Natural Product Syntheses
Part IV: Ring-Forming Reactions
36: Intramolecular Reactions
36.2 Intramolecular Ring-Forming Reactions via Covalent Catalysis
36.2.5 Lewis Base Catalysis of Tertiary Amines or Phosphines
36.3 Intramolecular Ring-Forming Reactions by Non-Covalent Catalysis
36.3.1 Brønsted Acid Catalysis
36.3.2 Bifunctional Catalysis
37: Formation of 3-, 4- and 5-Membered Cycles by Intermolecular Reactions
37.2 Organocatalytic Asymmetric Synthesis of Five-Membered Cycles
37.2.1 Synthesis of Five-Membered Cycles via [3+2] Cycloadditions
37.2.2 Five-Membered Cycles via Domino Reactions
37.3 Organocatalytic Asymmetric Synthesis of Four-Membered Cycles
37.4 Organocatalytic Asymmetric Synthesis of Three-Membered Cycles
37.4.1 Synthesis of Cyclopropanes
37.4.2 Synthesis of Aziridines
38: Diels-Alder and Hetero-Diels–Alder Reactions
38.2 Organocatalytic Diels–Alder Reaction
38.2.1 Chiral Secondary or Primary Amines as Catalysts
38.2.2 Chiral Brønsted Acids Catalysts (Hydrogen-Bonding or Brønsted Acid Activation)
38.2.3 Chiral Bifunctional Catalysts
38.3 Organocatalysis of Oxa-Hetero-Diels–Alder Reaction
38.3.1 Chiral Bases as Catalysts
38.3.2 Chiral Brønsted Acids as Catalysts
38.3.3 Chiral N-Heterocyclic Carbenes as Catalysts
38.4 Organocatalysis of Aza-Hetero-Diels–Alder Reaction
38.4.1 Chiral Carbenes as Catalysts
38.4.2 Chiral Amines as Catalysts
38.4.3 Chiral Brønsted Acids as Catalysts
Part V: Increasing Complexity
39: Organocatalytic Radical and Electron Transfer Reactions
39.2 Chemically Induced Oxidative Electron-Transfer Reactions
39.2.1 Oxamination Reactions
39.2.2 Additions to Olefins and Alkynes
39.2.3 Asymmetric Intermolecular Allylation of Aldehydes
39.2.4 Asymmetric Allylation of Ketones
39.2.5 Intramolecular Asymmetric Allylations
39.2.8 Carbo-Oxidation of Styrenes
39.2.9 Polyene Cyclizations
39.2.10 Intramolecular α-Arylation
39.2.11 Cascade Cycloadditions
39.2.12 Asymmetric Nitroalkylation of Aldehydes
39.3 Photoredox Catalysis
39.3.1 α-Alkylation of Aldehydes
39.3.2 α-Benzylation of Aldehydes
39.3.3 α-Trifluoromethylation of Aldehydes
39.4 Photochemical Asymmetric Synthesis
40: Organocatalytic Sigmatropic Reactions
40.2 Steglich and Related Rearrangements
40.3 1,3-Sigmatropic Rearrangements
40.4 1,4-Sigmatropic Rearrangements
40.5 2,3-Sigmatropic Rearrangements
40.6 3,3-Sigmatropic Rearrangements
40.7 Aza-Petasis–Ferrier Rearrangement
40.8 Pinacol and Related Rearrangements
41: Regio- and Position Selective Reactions and Desymmetrizations
41.2 Kinetic Resolution of Alcohols
41.2.1 Acylation-Based Processes
41.2.2 Phosphorylation-Based Process
41.2.3 Sulfonylation- and Sulfinylation-Based Process
41.2.4 Silylation-Based Process
41.3 Kinetic Resolution of Amines
41.3.1 Acylation-Based Process
42: Three or More Components Reactions (Single Catalyst Systems)
42.1 General Introduction
42.2 Covalent Modes of Catalysis – Developing MCRs by Asymmetric Aminocatalysis
42.2.1 Asymmetric MCRs Based on a Single Aminocatalytic Step
42.2.2 Asymmetric MCRs Based on Two Aminocatalytic Steps
42.2.3 Asymmetric MCRs Based on Three or More Aminocatalytic Steps
42.2.4 One-Pot Asymmetric MCRs for the Preparation of Active Pharmaceutical Ingredients
42.3 Non-Covalent Modes of Catalysis
42.3.3 Strecker Reactions
42.3.4 Kabachnik–Fields Reaction
42.3.7 Reductive Amination
42.3.8 Hantzsch Dihydropyridine and Related Reactions
42.3.9 Biginelli Reactions
42.3.10 1,3-Dipolar (Huisgen) Cycloaddition Reactions
42.3.11 Diels–Alder Reactions
42.4 Merging Covalent and Non-Covalent Activation Modes
43: Multi-Catalyst Systems
43.2 Combinational Use of Dual Brønsted Acids
43.3 Combinational Use of Chiral Brønsted Acid and Chiral or Achiral Lewis Base
43.4 Carbene-Based Dual Organocatalysis
43.5 Amino Catalyst-Based Cooperative Catalysis with Multifarious Co-Catalysts
44: Organocatalysis in Total Synthesis
44.2 Aminocatalysis in Natural Product Synthesis
44.2.2 Dienamine Catalysis
44.2.4 Organocascade Catalysis: Combinations of Enamine and Iminium Catalysis
44.3 Hydrogen Bond Catalysis in Total Synthesis
44.3.2 (Thio)urea Organocatalyzed Processes
44.4 Cinchona Alkaloids in Total Synthesis
44.5 Phase-Transfer Catalysis in Target Molecule Synthesis
44.6 Industrial Applications of Organocatalysis
44.6.1 Aminocatalysis in the Industrial Sector
44.6.2 Thiourea Catalysis at the Industrial Scale
44.6.3 Cinchona Alkaloids at the Industrial Level
44.6.4 Phase-Transfer Catalysis in Industry
Comprehensive Enantioselective Organocatalysis
：Catalysts, Reactions, and Applications, 3 Volume Set
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