Hydrogen Bonding in Organic Synthesis

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  • Format: Hardcover
  • Copyright: 2009-11-23
  • Publisher: Vch Pub

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This first comprehensive overview of the rapidly growing field emphasizes the use of hydrogen bonding as a tool for organic synthesis, especially catalysis. As such, it covers such topics as enzyme chemistry, organocatalysis and total synthesis, all unified by the unique advantages of hydrogen bonding in the construction of complex molecules from simple precursors. Providing everything you need to know, this is a definite must for every synthetic chemist in academia and industry.

Author Biography

After a postdoctoral stay with K. C. Nicolaou, Petri Pihko joined the faculty of Helsinki University of Technology, where his group was awarded the "Outstanding Junior Research Group" award of the University in 2004. His current research interests include organocatalysis, catalyst design, and total synthesis.

Table of Contents

Prefacep. ix
List of Contributorsp. xi
Introductionp. 1
Introductionp. 1
Hydrogen Bonding in Organic Synthesisp. 3
Referencesp. 4
Hydrogen-Bond Catalysis or Brønsted-Acid Catalysis? General Considerationsp. 5
Introductionp. 5
What is the Hydrogen Bond?p. 6
Hydrogen-Bond Catalysis or Brønsted-Acid Catalysisp. 7
Brønsted-Acid Catalysisp. 9
Hydrogen-Bond Catalysisp. 11
Referencesp. 13
Computational Studies of Organocatalytic Processes Based on Hydrogen Bondingp. 15
Introductionp. 15
Catalytic Functions of Hydrogen Bondsp. 18
Dynamic Kinetic Resolution (DKR) of Azlactones-Thioureas Can Act as Oxyanion Holes Comparable to Serine Hydrolasesp. 19
The Calculated Reaction Path of the Alcoholytic Ring Opening of Azlactonesp. 19
How Hydrogen Bonds Determine the Enantioselectivity of the Alcoholytic Azlactone Openingp. 23
On the Bifunctionality of Chiral Thiourea-Tert-Amine-Based Organocatalysts: Competing Routes to C-C Bond Formation in a Michael Additionp. 25
Dramatic Acceleration of Olefin Epoxidation in Fluorinated Alcohols: Activation of Hydrogen Peroxide by Multiple Hydrogen Bond Networksp. 29
Hydrogen Bond Donor Features of HFIPp. 30
The Catalytic Activity of HFIP in the Epoxidation Reactionp. 30
TADDOL-Promoted Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with Benzaldehyde-Another Example for Catalysis by Cooperative Hydrogen Bondingp. 37
Epilogp. 40
Referencesp. 41
Oxyanion Holes and Their Mimicsp. 43
Introductionp. 43
What are Oxyanion Holes?p. 44
Contributions of Oxyanion Holes to Catalysisp. 44
Properties of Hydrogen Bonds of Oxyanion Holesp. 47
A More Detailed Description of the Two Classes of Oxyanion Holes in Enzymesp. 49
A Historical Perspectivep. 49
Oxyanion Holes with Tetrahedral Intermediatesp. 52
Oxyanion Holes with Enolate Intermediatesp. 56
Examples of Enolate Oxyanion Holesp. 58
Oxyanion Hole Mimicsp. 61
Mimics of Enzymatic Oxyanion Holes and Similar Systemsp. 61
Utilization of Oxyanion Holes in Enzymes for Other Reactionsp. 64
Concluding Remarksp. 67
Acknowledgmentsp. 67
Referencesp. 67
Brønsted Acids, H-Bond Donors, and Combined Acid Systems in Asymmetric Catalysisp. 73
Introductionp. 73
Brønsted Acid (Phosphoric Acid and Derivatives)p. 75
Binapdiylphosphoric Acidsp. 75
Mannich Reactionp. 75
Hydrophosphonylationp. 78
Friedel-Craftsp. 79
Diels-Alderp. 83
Miscellaneous Reactionsp. 85
Nonimine Electrophilesp. 89
Transfer Hydrogenationp. 89
Nonbinol-Based Phosphoric Acidsp. 91
N-Trifiyl Phosphoramidep. 95
Asymmetric Counteranion-Directed Catalysisp. 98
N-H Hydrogen Bond Catalystsp. 99
Guanidine Organic Basep. 99
Ammonium Salt Catalysisp. 106
Chiral Tetraaminophosphonium Saltp. 109
Combined Acid Catalysisp. 109
Brønsted-Acid-Assisted Brønsted Acid Catalysisp. 110
Diol Activation of Carbonyl Electrophilesp. 111
Diol Activation of Other Electrophilesp. 116
Miscellaneous BBA and Related Systemsp. 120
Lewis-Acid-Assisted Brønsted Acid Catalysisp. 122
Brønsted-Acid-Assisted Lewis Acid Catalysis (Cationic Oxazaborolidine)p. 126
Diels-Alder Reactionsp. 126
Miscellaneous Reactionsp. 132
Referencesp. 136
(Thio)urea Organocatalystsp. 141
Introduction and Backgroundp. 141
Synthetic Applications of Hydrogen-Bonding (Thio)urea Organocatalystsp. 149
Nonstereoselective (Thio)urea Organocatalystsp. 149
Privileged Hydrogen-Bonding N, N'-bis-[3, 5-(Trifluoromethyl)phenyl]thioureap. 149
Miscellaneous Nonstereoselective (Thio)urea Organocatalystsp. 174
Stereoselective (Thio)urea Organocatalystsp. 185
(Thio)ureas Derived From Trans-l,2-Diaminocyclohexane and Related Chiral Primary Diaminesp. 185
(Thio)ureas Derived from Cinchona Alkaloidsp. 253
(Thio)urea Catalysts Derived from Chiral Amino Alcoholsp. 288
Binaphthyl-Based (Thio)urea Derivativesp. 296
Guanidine-Based Thiourea Derivativesp. 307
Saccharide-Based (Thio)urea Derivativesp. 315
Miscellaneous Stereoselective (Thio)urea Derivativesp. 324
Summary and Outlookp. 330
Acknowledgmentp. 332
Abbreviations and Acronymsp. 333
Referencesp. 336
Appendix: Structure Indexp. 345
Highlights of Hydrogen Bonding in Total Synthesisp. 353
Introductionp. 353
Intramolecular Hydrogen Bonding in Total Synthesesp. 353
Thermodynamic Control of Stereochemistryp. 353
Pinnatoxin Ap. 353
Azaspiracid-1p. 355
Kinetic Control Stereochemistryp. 355
Pancratistatinp. 355
Tunicamycinsp. 357
Callystatinp. 358
Resorcylidesp. 359
Strychnofolinep. 361
Asialo GM1p. 361
Activation/Deactivation of Reactionsp. 362
Rishirilide Bp. 362
2-Desoxystemodionep. 363
Leucascandrolide Ap. 363
Azaspirenep. 364
Intermolecular Hydrogen Bondings in Total Synthesesp. 365
Henbest Epoxidationp. 365
Epoxyquinolsp. 366
Epoxide-Opening Cascadesp. 367
Conclusionsp. 369
Referencesp. 369
Indexp. 373
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