Organic Synthesis Strategy and Control

by Wyatt, Paul; Warren, Stuart

• ISBN13: 9780471489405
• ISBN10: 0471489409
• Edition: 1st
• Format: Hardcover
• Copyright: 2007-06-05
• Publisher: WILEY

Summary

Organic Synthesis: Strategy and Control is the long-awaited sequel to Stuart Warren's bestseller Organic Synthesis: The Disconnection Approach, which looked at the planning behind the synthesis of compounds. This unique book now provides a comprehensive, practical account of the key concepts involved in synthesising compounds and focuses on putting the planning into practice.The two themes of the book are strategy and control: solving problems either by finding an alternative strategy or by controlling any established strategy to make it work. The book is divided into five sections that deal with selectivity, carbon-carbon single bonds, carbon-carbon double bonds, stereochemistry and functional group strategy. A comprehensive, practical account of the key concepts involved in synthesising compounds Takes a mechanistic approach, which explains reactions and gives guidelines on how reactions might behave in different situations Focuses on reactions that really work rather than those with limited application Contains extensive, up-to-date references in each chapterStudents and professional chemists familiar with Organic Synthesis: The Disconnection Approach will enjoy the leap into a book designed for chemists at the coalface of organic synthesis.

Author Biography

Paul Wyatt, Senior Lecturer and Director of Undergraduate Studies, School of Chemistry, University of Bristol, UK and Stuart Warren, Reader in Organic Chemistry, Department of Chemistry, University of Cambridge, UK.

Table of Contents

Preface

Introduction: Selectivity

Planning Organic Syntheses: Tactics, Strategy, and Control

Chemoselectivity

Regioselectivity: Controlled Aldol Reactions

Stereoselectivity: Stereoselective Aldol Reactions

Alternative Strategies for Enone Synthesis

Choosing a Strategy : The Synthesis of cyclopentenones

Making Carbon-Carbon Bonds

The Ortho Strategy for Aromatic Compounds

I'-Complexes of Metals

Controlling the Michael Reaction

Specific Enol Equivalents

Extended Enolates

Allyl Anions

Homoenolates

Acyl Anion Equivalents

Carbon-Carbon Double Bonds

Synthesis of Double Bonds of Defined Stereochemistry

Stereo-Controlled Vinyl Anion Equivalents

Electrophilic Attack on Alkenes

Vinyl Cations: Palladium-Catalysed C-C Coupling

Allyl Alcohols: Allyl Cation Equivalents (and More)

Stereochemistry

Control of Stereochemistry - Introduction

Controlling Relative Stereochemistry

Resolution

The Chiral Pool

Asymmetric Induction I: Reagent-Based Strategy

Asymmetric Induction II: Asymmetric Catalysis: Formation of C-O and C-N Bonds

Asymmetric Induction III: Asymmetric Catalysis: Formation of C-H and C-C Bonds

Asymmetric Induction IV: Substrate-Based Strategy

Kinetic Resolution

Enzymes: Biological Methods in Asymmetric Synthesis

New Chiral Centres from Old - Enantiomerically Pure Compounds & Sophisticated Syntheses

Strategy of Asymmetric Synthesis

Functional Group Strategy

Functionalisation of Pyridine

Oxidation of Aromatic Compounds, Enols and Enolates

Functionality and Pericyclic Reactions: Nitrogen Heterocycles by Cycloadditions and Sigmatropic Rearrangements

Synthesis and Chemistry of Azoles and other Heterocycles with Two or more Heteroatoms

Tandem Organic Reactions

General References

Index

Table of Contents provided by Publisher. All Rights Reserved.