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Modern Organic Synthesis - An Introduction

George S. Zweifel, Michael H. Nantz

Softcover, 504 Pages
1st Edition, 2007
ISBN: 978-0-716-77266-8
W. H. Freeman


Written for the organic synthesis portion of the advanced organic chemistry course (taken by seniors and graduate students), Zweifel and Nantz’s concise new text covers the essentials with exceptional coherence and clarity without bogging students down with too much unnecessary material.

Editorial Review

"Modern Organic Synthesis - An Introduction" is aimed at advanced students who have already completed an introductory course in organic chemistry and who would now like to deepen their understanding. With this basic knowledge as a foundation, the authors attempt to define important tactics and reactions as well as reagents, a goal which they attain quite well. Chapters on synthetic design and stereochemical considerations in synthesis planning, as well as ideas for the protection of functional groups, provide well-focused illustrations of fundamental approaches. The language is readily understandable, and the topics are well supported by interesting concrete examples. What stands out is that the authors make a substantial effort to mention a variety of reaction conditions and reagents with which delicate transformations can be carried out selectively. The selective protection of polyfunctional molecules, or examples of the oxidation and reduction of functional groups in the presence of other groups, are described in detail.

In comparison to old-fashioned textbooks that are strictly organized into sections by substance class or reaction mechanism, the chapters in this book are more freely arranged and are self-contained. The diversity of topics is not as broad as in other organic textbooks for advanced students, some of which exceed one thousand pages. But the authors have clearly succeeded in selecting important themes and focusing on an assortment of synthesis variants.

In addition, the book does not require a linear reading; rather, one can delve deeply into specific topics of interest. In "Modern Organic Synthesis - An Introduction", one can find several examples and absorbing commentary that help to deepen one’s existing comprehension and to link it with detailed knowledge. Since the authors often achieve this by providing concrete advice on reagents and reaction conditions backed up by literature citations, the reader will also find it beneficial to consult this work in addressing specific synthesis problems. In this way, "Modern Organic Synthesis - An Introduction" is a worthwhile book for advanced students, who will still find it useful in their later professional careers.


1. Synthetic Design
1.1 Retrosynthetic Design
1.2 Reversal of the Carbonyl Group Polarity (Umpolung)
1.3 Steps in Planning a Synthesis
1.4 Choice of Sythetic Method
1.5 Domino Reactions
1.6 Computer-Assisted Retrosynthetic Analysis

2. Stereochemical Considerations in Planning Synthesis
2.1 Conformational Analysis
2.2 Evaluation of Nonbonded Interactions
2.3 Six-Member Hetercyclic Systems
2.4 Polycyclic Ring Systems
2.5 Cyclohexyl Systems with sp2-Hybridized Atoms
2.6 Significant Energy Difference
2.7 Computer-Assisted Molecular Modeling
2.8 Reactivity and Product Determination as a Function of Conformation

3. The Concept of Protecting Functional Groups
3.1 Protection of NH Groups
3.2 Protection of OH Groups of Alcohols
3.3 Protection of Diols as Acetals
3.4 Protection of Carbonyl Groups in Aldehydes and Ketones
3.5 Protection of the Carboxyl Group
3.6 Protection of Double Bonds
3.7 Protection of Triple Bonds

4. Functional Group Transformations: Oxidation and Reduction
4.1 Oxidation of Alcohols to Aldehydes and Ketones
4.2 Reagents and Procedures of Alcohol Oxidation
4.3 Chemoselective Agents for Oxidizing Alcohols
4.4 Oxidation of Acyloins
4.5 Oxidation of Tertiary Allylic Alcohols
4.6 Oxidative Procedures to Carboxylic Acids
4.7 Allylic Oxidation of Alkenes
4.8 Terminology for Reduction of Carbonyl Compounds
4.9 Nucleophilic Reducing Agents
4.10 Electrophilic Reducing Agents
4.11 Regio- and Chemoselective Agents
4.12 Diastereoselective Reductions of Cyclic Ketones
4.13 Inversion of Secondary Alcohol Stereochemistry
4.14 Diastereofacial Selectivity in Acyclic Systems
4.15 Enantioselective Reductions

5. Functional Group Transformations: The Chemistry of Carbon-Carbon pi-Bonds and Related Reactions
5.1 Reactions of Carbon-Carbon Double Bonds
5.2 Reactions of Carbon-Carbon Triple Bonds

6. Formation of Carbon-Carbon Single Bonds
6.1 1,3-Dicarbonyl and Related Compounds
6.2 Direct Alkylation of Simple Enolates
6.3 Cyclization Reactions--Baldwin's Rules for Ring Closure
6.4 Stereochemistry of Cyclic Ketone Alkelation
6.5 Imine and Hydrazone Anions
6.6 Enamines
6.7 The Aldol Reaction
6.8 Condensation Reactions of Enols and Enolates
6.9 Robinson Annulation

7. Formation of Carbon-Carbon Bonds Via Organometallic Reagents
7.1 Organolithium Reagents
7.2 Organomagnesium Reagents
7.3 Organotitanium Reagents
7.4 Organocerium Reagents
7.5 Organocopper Reagents
7.6 Organochromium Reagents
7.7 Organozinc Reagents
7.8 Organoboron Reagents
7.9 Organosilicon Reagents
7.10 Palladium-Catalyzed Coupling Reactions

8. Formation of Carbon-Carbon pi-Bonds
8.1 Formation of Carbon-Carbon Double Bonds
8.2 Formation of Carbon-Carbon Triple Bonds

9. Synthesis of Carbocyclic Systems
9.1 Intramolecular Free Radical Cyclizations
9.2 Cation-pi Cyclizations
9.3 Pericyclic Reactions
9.4 Ring-Closing Olefin Metathesis (RCM)

10. The Art of Synthesis

Answers to Select End-of-Chapter Problems