Synopses & Reviews
Taking a reagent-based approach, Modern Organic Synthesis manages to clearly present the fundamental principles of this challenging subject in a clear manner that avoids overwhelming students. Bullet lists and end of chapter problems help students get to grips with tricky concepts and the book's practical, concise approach will also make it a useful handbook for researchers. Up-to-date references and an accompanying solutions manual, make this an ideal compliment to advanced Organic Chemistry courses.
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.
Table of Contents
1. Synthetic Design
1.1 Retrosynthetic Design1.2 Reversal of the Carbonyl Group Polarity (Umpolung)
1.3 Steps in Planning a Synthesis1.4 Choice of Sythetic Method1.5 Domino Reactions1.6 Computer-Assisted Retrosynthetic Analysis 2. Stereochemical Considerations in Planning Synthesis
2.1 Conformational Analysis2.2 Evaluation of Nonbonded Interactions2.3 Six-Member Hetercyclic Systems2.4 Polycyclic Ring Systems2.5 Cyclohexyl Systems with sp2-Hybridized Atoms2.6 Significant Energy Difference2.7 Computer-Assisted Molecular Modeling2.8 Reactivity and Product Determination as a Function of Conformation 3. The Concept of Protecting Functional Groups
3.1 Protection of NH Groups3.2 Protection of OH Groups of Alcohols3.3 Protection of Diols as Acetals3.4 Protection of Carbonyl Groups in Aldehydes and Ketones3.5 Protection of the Carboxyl Group3.6 Protection of Double Bonds3.7 Protection of Triple Bonds 4. Functional Group Transformations: Oxidation and Reduction
4.1 Oxidation of Alcohols to Aldehydes and Ketones4.2 Reagents and Procedures of Alcohol Oxidation4.3 Chemoselective Agents for Oxidizing Alcohols4.4 Oxidation of Acyloins4.5 Oxidation of Tertiary Allylic Alcohols4.6 Oxidative Procedures to Carboxylic Acids4.7 Allylic Oxidation of Alkenes4.8 Terminology for Reduction of Carbonyl Compounds4.9 Nucleophilic Reducing Agents4.10 Electrophilic Reducing Agents4.11 Regio- and Chemoselective Agents4.12 Diastereoselective Reductions of Cyclic Ketones4.13 Inversion of Secondary Alcohol Stereochemistry4.14 Diastereofacial Selectivity in Acyclic Systems4.15 Enantioselective Reductions 5. Functional Group Transformations: The Chemistry of Carbon-Carbon pi-Bonds and Related Reactions
5.1 Reactions of Carbon-Carbon Double Bonds5.2 Reactions of Carbon-Carbon Triple Bonds 6. Formation of Carbon-Carbon Single Bonds
6.1 1,3-Dicarbonyl and Related Compounds6.2 Direct Alkylation of Simple Enolates6.3 Cyclization Reactions--Baldwin's Rules for Ring Closure6.4 Stereochemistry of Cyclic Ketone Alkelation6.5 Imine and Hydrazone Anions6.6 Enamines6.7 The Aldol Reaction6.8 Condensation Reactions of Enols and Enolates6.9 Robinson Annulation 7. Formation of Carbon-Carbon Bonds Via Organometallic Reagents
7.1 Organolithium Reagents7.2 Organomagnesium Reagents7.3 Organotitanium Reagents7.4 Organocerium Reagents7.5 Organocopper Reagents7.6 Organochromium Reagents7.7 Organozinc Reagents7.8 Organoboron Reagents7.9 Organosilicon Reagents7.10 Palladium-Catalyzed Coupling Reactions 8. Formation of Carbon-Carbon pi-Bonds
8.1 Formation of Carbon-Carbon Double Bonds8.2 Formation of Carbon-Carbon Triple Bonds 9. Synthesis of Carbocyclic Systems
9.1 Intramolecular Free Radical Cyclizations9.2 Cation-pi Cyclizations9.3 Pericyclic Reactions9.4 Ring-Closing Olefin Metathesis (RCM) 10. The Art of Synthesis
AbbreviationsAnswers to Select End-of-Chapter ProblemsIndex