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.
Petri Pihko was born in 1971 in Oulu, Finland. He became interested in chemistry several years before entering the university, assisted by inspiring teachers, Maija Aksela (currently a Professor of Chemical Education at the University of Helsinki) and Prof. Hans Krieger, who also taught him organic chemistry at the University of Oulu before his retirement. Petri Pihko then joined the research group of Professor Ari Koskinen, graduating with a Ph.D. in 1999. Between 1999 and 2001, he enjoyed nearly two years of a wonderful time as a postdoctoral associate with Professor K. C. Nicolaou at the Scripps Research Institute in La Jolla, California, USA. In 2001, he joined the faculty of Helsinki University of Technology (TKK), and in 2008, his research group moved to the University of Jyvaskyla, Finland. His research interests include organocatalysis, catalyst design, and total synthesis of natural products.
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