Preface to the First Edition
Preface to the Second Edition
Chapter 1: Synthetic Design
1.1 Retrosynthetic Analysis
1.2 Reversal of the Carbonyl Group Polarity (Umpolung)
1.3 Steps in Planning a Synthesis
1.4 Choice of Synthetic Method
1.5 Domino Reactions (also called Cascade or Tandem Reactions)
1.6 Computer-Assisted Retrosynthetic Analysis
References
Chapter 2: Stereochemical Considerations in Planning Syntheses
2.1 Conformational Analysis
2.2 Evaluation of Non-Bonded Interactions
2.3 Six-Membered Heterocyclic 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
References
Chapter 3: The Concept of Protecting Functional Groups
3.1 Protection of N–H- Groups
3.2 Protection of OH-Groups
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
References
Chapter 4: Functional Group Transformations
4.1 Oxidation of Alcohols to Aldehydes and Ketones
4.2 Reagents and Procedures for Alcohol Oxidation
4.3 Chemoselective Oxidizing Agents
4.4 Oxidation of Acyloins
4.5 Oxidation of Tertiary Allylic Alcohols (The Babler Oxidation)
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 Reductions
4.12 Diastereoselective Reductions of Cyclic Ketones
4.13 Inversion of Secondary Alcohol Stereochemistry (The Mitsunobu Reaction)
4.14 Diastereofacial Selectivity in Acyclic Systems
4.15 Enantioselective Reductions
References
Chapter 5: Functional Group Transformations
5.1 Reactions of Carbon–Carbon Double Bonds
5.2 Reactions of Carbon-Carbon Triple Bonds
References
Chapter 6: Formation of Carbon–Carbon Single Bonds Via Enolate Anions
6.1 1,3-Dicarbonyl Compounds
6.2 Direct Alkylation of Enolates
6.3 Cyclization Reactions — Baldwin's Rules for Ring Closure
6.4 Stereochemistry of Cyclic Ketone Alkylation
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
References
Chapter 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 Organogold chemistry
References
Chapter 8: Palladium- Catalyzed Coupling Reactions
8.1 Palladium Oxidation State
8.2 Organic Synthesis with Palladium(0) Complexes
8.3 The Heck Reaction — Palladium(0)-Catalyzed Olefin Insertion Reactions
8.4 Palladium-Catalyzed Cross-Coupling with Organometallic Reagents
8.5 Cross-Coupling Reactions Involving sp-Carbons
8.6 The Trost–Tsuji Reaction
References
Chapter 9: Formation of Carbon-Carbon π-Bonds
9.1 Formation of Carbon-Carbon Double Bonds
9.2 Formation of Carbon-Carbon Triple Bonds
References
Chapter 10: Syntheses of Carbocyclic Systems
10.1 Intramolecular Free Radical Cyclizations
10.2 Cation-π Cyclizations
10.3 Pericyclic Reactions
10.4 Ring-Closing Olefin Metathesis (RCM)
References
(leitura online e APP)
