Hydrogen Bonding in Organic Synthesis (eBook)

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 Jyväskylä, 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