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Hydrogen Bonding in Organic Synthesis

Hydrogen Bonding in Organic Synthesis

Petri M. Pihko (Editor)

ISBN: 978-3-527-62784-4

Nov 2009

395 pages

Select type: O-Book

Description

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.
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
""Hydrogen Bonding in Organic Synthesis is well organized and delivered in a way easy for every synthetic chemist in academia and industry to understand."" (Current Engineering Practice, 1 November 2010)

“The material is well-organized and recent.” (JACS Reviews, 2010)