Hydrogen Bonding in Organic Synthesis

Abstract

Preface INTRODUCTION Introduction Hydrogen Bonding in Organic Synthesis HYDROGEN-BOND CATALYSIS OR BRONSTED-ACID CATALYSIS? GENERAL CONSIDERATIONS Introduction What is the Hydrogen Bond? Hydrogen-Bond Catalysis or Bronsted-Acid Catalysis Bronsted-Acid Catalysis Hydrogen-Bond Catalysis COMPUTATIONAL STUDIES OF ORGANOCATALYTIC PROCESSED BASED ON HYDROGEN BONDING Introduction Dynamic Kinetic Resolution (DKR) of Azlactones-Thioureas Can Act as Oxyanion Holes Comparable to Serine Hydrolases On the Bifunctionality of Chiral Thiourea-Tert-Amine-Based Organocatalysts: Competing Routes to C-C Bond Formation in a Michael Addition Dramatic Acceleration of Olefin Epoxidation in Fluorinated Alcohols: Activation of Hydrogen Peroxide by Multiple Hydrogen Bond Networks TADDOL-Promoted Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with Benzaldehyde - Another Example for Catalysis by Cooperative Hydrogen Bonding Epilog OXYANION HOLES AND THEIR MIMICS Introduction What are Oxyanion Holes? A More Detailed Description of the Two Classes of Oxyanion Holes in Enzymes Oxyanion Hole Mimics Concluding Remarks BRONSTED ACIDS, H-BOND DONORS, AND COMBINED ACID SYSTEMS IN ASYMMETRIC CATALYSIS Introduction Bronsted Acid (Phosphoric Acid and Derivatives) N-H Hydrogen Bond Catalysts Combined Acid Catalysis (THIO)UREA ORGANOCATALYSTS Introduction and Background Synthetic Applications of Hydrogen-Bonding (Thio)urea Organocatalysts Summary and Outlook HIGHLIGHTS OF HYDROGEN BONDING IN TOTAL SYNTHESIS Introduction Intramolecular Hydrogen Bonding in Total Syntheses Intermolecular Hydrogen Bondings in Total Syntheses Conclusions