Preface

Acknowledgment and Personal Statement

Introduction

Chapter 1. Alkylation of Enolates and Other Carbon Nucleophiles

Introduction

1.1. Generation and Properties of Enolates and Other Stabilized Carbanions

1.1.1. Generation of Enolates by Deprotonation

1.1.2. Regioselectivity and Stereoselectivity in Enolate Formation from Ketones and Esters

1.1.3. Other Means of Generating Enolates

1.1.4. Solvent Effects on Enolate Structure and Reactivity

1.2. Alkylation of Enolates

1.2.1. Alkylation of Highly Stabilized Enolates

1.2.2. Alkylation of Ketone Enolates

1.2.3. Alkylation of Aldehydes, Esters, Carboxylic Acids, Amides, and Nitriles

1.2.4. Generation and Alkylation of Dianions

1.2.5. Intramolecular Alkylation of Enolates

1.2.6. Control of Enantioselectivity in Alkylation Reac:ions

1.3. The Nitrogen Analogs of Enols and Enolates: Enamines and Imine Anions

General References

Problems

Chapter 2. Reactions of Carbon Nucleophiles with Carbonyl Compounds

Introduction

2.1. Aldol Addition and Condensation Reactions

2.1.1. The General Mechanism

2.1.2. Control of Regio- and Stereoselectivity of Aldol Reactions of Aldehydes and Ketones

2.1.3. Aldol Addition Reactions of Enolates of Esters and Other Carbonyl Derivatives

2.1.4. The Mukaiyama Aldol Reaction

2.1.5. Control of Facial Selectivity in Aldol and Mukaiyama Aldol Reactions

2.1.6. Intramolecular Aldol Reactions and the Robinson Annulation

2.2. Addition Reactions of Imines and Iminium Ions

2.2.1. The Mannich Reaction

2.2.2. Additions to N-Acyl Iminium Ions

2.2.3. Amine-Catalyzed Condensation Reactions

2.3. Acylation of Carbon Nucleophiles

2.3.1. Claisen and Dieckmann Condensation Reactions

2.3.2. Acylation of Enolates and Other Carbon Nucleophiles

2.4. Olefination Reactions of Stabilized Carbon Nucleophiles

2.4.1. The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophiles

2.4.2. Reactions of a-Trimethyisilylcarbanions with Carbonyl Compounds

2.4.3. The Julia Olefination Reaction

2.5. Reactions Proceeding by Addition-Cyclization

2.5.1. Sulfur Yiides and Related Nucleophiles

2.5.2. Nucleophilic Addition-Cyclization of ot-Haloesters

2.6. Conjugate Addition by Carbon Nucleophiles

2.6.1. Conjugate Addition of Enolates

2.6.2. Conjugate Addition with Tandem Alkylation

2.6.3. Conjugate Addition by Enolate Equivalents

2.6.4. Control of Facial Selectivity in Conjugate Addition Reactions

2.6.5. Conjugate Addition of Organometallic Reagents

2.6.6. Conjugate Addition of Cyanide Ion

General References

Problems

Chapter 3. Functional Group Interconversion by Substitution, Including Protection and Deprotection

Introduction

3.1. Conversion of Alcohols to Alkylating Agents

3.1.1. Sulfonate Esters

3.1.2. Halides

……

Chapter 4. Electrophilic Additions to Carbon-Carbon Multiple Bonds

Chapter 5. Reduction of Carbon-Carbon Multiple Bonds, Carbonyl Croups, and Other Functional Groups

Chapter 6. Concerted Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations

Chapter 7. Organometallic Compounds of Group I and II Metals

Chapter 8. Reactions Involving Transition Metals

Chapter 9. Carbon-Carbon Bond-Forming Reactions of Compounds of Boron, Silcon, and Tin

Chapter 10. Reactions Involving Carbocations, Carbenes, and Radicals and Reactive Intermediates

Chapter 11. Aromatic Substitution Reactions

Chapter 12. Oxidations

Chapter 13. Multistep Syntheses

References

Index