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Preface | p. ix |
List of Contributors | p. xi |
Introduction | p. 1 |
Introduction | p. 1 |
Hydrogen Bonding in Organic Synthesis | p. 3 |
References | p. 4 |
Hydrogen-Bond Catalysis or Brønsted-Acid Catalysis? General Considerations | p. 5 |
Introduction | p. 5 |
What is the Hydrogen Bond? | p. 6 |
Hydrogen-Bond Catalysis or Brønsted-Acid Catalysis | p. 7 |
Brønsted-Acid Catalysis | p. 9 |
Hydrogen-Bond Catalysis | p. 11 |
References | p. 13 |
Computational Studies of Organocatalytic Processes Based on Hydrogen Bonding | p. 15 |
Introduction | p. 15 |
Catalytic Functions of Hydrogen Bonds | p. 18 |
Dynamic Kinetic Resolution (DKR) of Azlactones-Thioureas Can Act as Oxyanion Holes Comparable to Serine Hydrolases | p. 19 |
The Calculated Reaction Path of the Alcoholytic Ring Opening of Azlactones | p. 19 |
How Hydrogen Bonds Determine the Enantioselectivity of the Alcoholytic Azlactone Opening | p. 23 |
On the Bifunctionality of Chiral Thiourea-Tert-Amine-Based Organocatalysts: Competing Routes to C-C Bond Formation in a Michael Addition | p. 25 |
Dramatic Acceleration of Olefin Epoxidation in Fluorinated Alcohols: Activation of Hydrogen Peroxide by Multiple Hydrogen Bond Networks | p. 29 |
Hydrogen Bond Donor Features of HFIP | p. 30 |
The Catalytic Activity of HFIP in the Epoxidation Reaction | p. 30 |
TADDOL-Promoted Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with Benzaldehyde-Another Example for Catalysis by Cooperative Hydrogen Bonding | p. 37 |
Epilog | p. 40 |
References | p. 41 |
Oxyanion Holes and Their Mimics | p. 43 |
Introduction | p. 43 |
What are Oxyanion Holes? | p. 44 |
Contributions of Oxyanion Holes to Catalysis | p. 44 |
Properties of Hydrogen Bonds of Oxyanion Holes | p. 47 |
A More Detailed Description of the Two Classes of Oxyanion Holes in Enzymes | p. 49 |
A Historical Perspective | p. 49 |
Oxyanion Holes with Tetrahedral Intermediates | p. 52 |
Oxyanion Holes with Enolate Intermediates | p. 56 |
Examples of Enolate Oxyanion Holes | p. 58 |
Oxyanion Hole Mimics | p. 61 |
Mimics of Enzymatic Oxyanion Holes and Similar Systems | p. 61 |
Utilization of Oxyanion Holes in Enzymes for Other Reactions | p. 64 |
Concluding Remarks | p. 67 |
Acknowledgments | p. 67 |
References | p. 67 |
Brønsted Acids, H-Bond Donors, and Combined Acid Systems in Asymmetric Catalysis | p. 73 |
Introduction | p. 73 |
Brønsted Acid (Phosphoric Acid and Derivatives) | p. 75 |
Binapdiylphosphoric Acids | p. 75 |
Mannich Reaction | p. 75 |
Hydrophosphonylation | p. 78 |
Friedel-Crafts | p. 79 |
Diels-Alder | p. 83 |
Miscellaneous Reactions | p. 85 |
Nonimine Electrophiles | p. 89 |
Transfer Hydrogenation | p. 89 |
Nonbinol-Based Phosphoric Acids | p. 91 |
N-Trifiyl Phosphoramide | p. 95 |
Asymmetric Counteranion-Directed Catalysis | p. 98 |
N-H Hydrogen Bond Catalysts | p. 99 |
Guanidine Organic Base | p. 99 |
Ammonium Salt Catalysis | p. 106 |
Chiral Tetraaminophosphonium Salt | p. 109 |
Combined Acid Catalysis | p. 109 |
Brønsted-Acid-Assisted Brønsted Acid Catalysis | p. 110 |
Diol Activation of Carbonyl Electrophiles | p. 111 |
Diol Activation of Other Electrophiles | p. 116 |
Miscellaneous BBA and Related Systems | p. 120 |
Lewis-Acid-Assisted Brønsted Acid Catalysis | p. 122 |
Brønsted-Acid-Assisted Lewis Acid Catalysis (Cationic Oxazaborolidine) | p. 126 |
Diels-Alder Reactions | p. 126 |
Miscellaneous Reactions | p. 132 |
References | p. 136 |
(Thio)urea Organocatalysts | p. 141 |
Introduction and Background | p. 141 |
Synthetic Applications of Hydrogen-Bonding (Thio)urea Organocatalysts | p. 149 |
Nonstereoselective (Thio)urea Organocatalysts | p. 149 |
Privileged Hydrogen-Bonding N, N'-bis-[3, 5-(Trifluoromethyl)phenyl]thiourea | p. 149 |
Miscellaneous Nonstereoselective (Thio)urea Organocatalysts | p. 174 |
Stereoselective (Thio)urea Organocatalysts | p. 185 |
(Thio)ureas Derived From Trans-l,2-Diaminocyclohexane and Related Chiral Primary Diamines | p. 185 |
(Thio)ureas Derived from Cinchona Alkaloids | p. 253 |
(Thio)urea Catalysts Derived from Chiral Amino Alcohols | p. 288 |
Binaphthyl-Based (Thio)urea Derivatives | p. 296 |
Guanidine-Based Thiourea Derivatives | p. 307 |
Saccharide-Based (Thio)urea Derivatives | p. 315 |
Miscellaneous Stereoselective (Thio)urea Derivatives | p. 324 |
Summary and Outlook | p. 330 |
Acknowledgment | p. 332 |
Abbreviations and Acronyms | p. 333 |
References | p. 336 |
Appendix: Structure Index | p. 345 |
Highlights of Hydrogen Bonding in Total Synthesis | p. 353 |
Introduction | p. 353 |
Intramolecular Hydrogen Bonding in Total Syntheses | p. 353 |
Thermodynamic Control of Stereochemistry | p. 353 |
Pinnatoxin A | p. 353 |
Azaspiracid-1 | p. 355 |
Kinetic Control Stereochemistry | p. 355 |
Pancratistatin | p. 355 |
Tunicamycins | p. 357 |
Callystatin | p. 358 |
Resorcylides | p. 359 |
Strychnofoline | p. 361 |
Asialo GM1 | p. 361 |
Activation/Deactivation of Reactions | p. 362 |
Rishirilide B | p. 362 |
2-Desoxystemodione | p. 363 |
Leucascandrolide A | p. 363 |
Azaspirene | p. 364 |
Intermolecular Hydrogen Bondings in Total Syntheses | p. 365 |
Henbest Epoxidation | p. 365 |
Epoxyquinols | p. 366 |
Epoxide-Opening Cascades | p. 367 |
Conclusions | p. 369 |
References | p. 369 |
Index | p. 373 |
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