Hydrogen Bonding in Organic Synthesis - Product Image

Hydrogen Bonding in Organic Synthesis

  • ID: 1198928
  • Book
  • 395 Pages
  • John Wiley and Sons Ltd
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Snow and ice, water droplets, and all key materials of life –– the double strands of DNA and all proteins –– are held together by intermolecular forces called hydrogen bonds. These bonds, although weaker than bonds within molecules, are still strong enough to chaperone molecules into desired orientations, allowing chemists to use them as tools to perform reactions with high selectivity. In addition, hydrogen bonding can lead to metal–free catalysts, thus saving chemicals and energy in an otherwise lengthy purification process while also reducing the heavy metal output in the environment.

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.

From the contents:

∗ Introduction

∗ Hydrogen Bond Catalysis or Brønsted Acid Catalysis? General Considerations

∗ Computational Studies of Organocatalytic Processes Based on Hydrogen Bonding

∗ Oxyanion holes and their mimics

∗ Brønsted Acids, H–Bond Donors, and Combined Acid Systems in Asymmetric Catalysis

∗ Hydrogen Bonding in Organic Synthesis – (Thio)urea Organocatalysts

∗ Highlights of Hydrogen Bonding in Total Synthesis

Providing everything you need to know, this is a definite must for every synthetic chemist in academia and industry.

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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
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"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)
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