Handbook on Syntheses of Amino Acids: General Routes for the Syntheses of Amino Acids (2010)

CHAPTER 1. INTRODUCTION 1.1 General Introduction 1,2 A Brief Summary of Trends in Amino Acid Synthesis 1.3 Industrial Synthesis 1.4 Amino Acid Properties 1.5 Absolute Configuration 1.6 Determination of Enantiomeric Purity 1.7 Determination of Enantiomeric Purity: NMR Analysis 1.8 Determination of Enantiomeric Purity: HPLC Chromatographic Analysis 1.9 Determination of Enantiomeric Purity: GC Chromatographic Analysis 1.10 Determination of Enantiomeric Purity: Capillary Electrophoresis Analysis 1.11 Determination of Enantiomeric Purity: TLC Chromatographic Analysis 1.12 Determination of Enantiomeric Purity: Mass Spectrometric Methods 1.13 Determination of Enantiomeric Purity: Other Methods CHAPTER 2. SYNTHESIS OF RACEMIC A-AMINO ACIDS: AMINATION AND CARBOXYLATION 2.1 Primordial Amino Acids 2.2 Addition of the Amino and Carboxy Groups to the Side Chain (Aminocarboxylation Reactions) 2.3 Addition of the Amino Group (Amination Reactions) 2.4 Addition of the Carboxyl Group (Carboxylation Reactions) 2.4.1 Electrophilic Carboxylation 2.4.2 Nucleophilic Carboxylation CHAPTER 3. SYNTHESIS OF RACEMIC -AMINO ACIDS: INTRODUCTION OF THE SIDE CHAIN 3.1 Introduction 3.2 Alkylation of Aminomalonic Acids 3.3 Alkylation of Aminocyanoacetic Acids 3.4 Alkylation of Schiff Bases 3.5 Alkylation of Isocyanoacetates 3.6 Alkylation of Other Activated Glycine Equivalents 3.7 Alkylation of Non-Activated Glycines 3.8 Alkylation of Glycine Equivalents via Other Methods 3.9 Alkylation of an Electrophilic Glycine Equivalent 3. 10 Radical Alkylations CHAPTER 4. SYNTHESIS AND ELABORATION OF DIDEHYDRO AMINO ACIDS 4.1 Introduction 4.2 Sythesis of Didehydroamino Acids 4.3 Reactions of Didehydroamino Acids CHAPTER 5. SYNTHESIS OF OPTICALLY ACTIVE A-AMINO ACIDS: EXTENSION OF ACHIRAL METHODS - AMINATION AND CARBOXYLATION REACTIONS 5.1 Introduction 5.2 Asymmetric Aminocarboxylation Reaction 5.3 Asymmetric Amination Reactions 5.4 Asymmetric Carboxylation Reactions CHAPTER 6. SYNTHESIS OF OPTICALLY ACTIVE AMINO ACIDS: EXTENSION OF ACHIRAL METHODS - INTRODUCTION FO THE SIDE CHAIN TO ACYCLIC SYSTEMS 6.1 Introduction 6.2 Asymmetric Alkylations of Glycine Enolates 6.3 Reactions of Isocyanocarboxylate Enolates 6.4 Alkylations of Schiff Bases of Glycine or Other Amino Acids 6.5 Asymmetric Alkylations of Electrophilic Glycine Equivalents 6.6 Asymmetric Radical Alkylations of Acyclic Glycine Equivalents CHAPTER 7. SYNTHESIS OF OPTICALLY ACTIVE A-AMINO ACIDS: ALKYLATION OF CYCLIC CHIRAL TEMPLATES 7.1 Introduction 7.2 Schollkopf Bis-lactim Ether 7.3 Piperazine-2,5-dione 7.4 Morpholine-2,5-dione 7.5 Williams Oxazinone (5,6-diphenyl-1,4-oxazin-2-one, 5,6-diphenylmorpholin-2-one) 7.6 Other Oxazinones (1,4-oxazin-2-one, morpholin-2-one) 7.7 Seebach Oxazolidin-5-one 7.8 Oxazolidin-2-ones 7.9 Seebach Imidazolidin-4-one 7.10 Other Imidazolidinones and Related Templates 7.11 Cyclic Metal Complexes 7.12 Other Cyclic Chiral Templates CHAPTER 8. SYNTHESIS OF OPTICALLY ACTIVE A-AMINO ACIDS: OPENING OF SMALL RING SYSTEMS 8.1 Introduction 8.2 Aziridines 8.3 Azirines 8.4 Epoxides 8.5 b-Lactams CHAPTER 9. SYNTHESIS OF OPTICALLY ACTIVE A-AMINO ACIDS: ELABORATION OF AMINO ACIDS OTHER THAN SERINE 9.1 Introduction 9.2 Synthesis of Optically Active Amino Acids from Aspartic Acid 9.3 Synthesis of Optically Active Amino Acids from Glutamic Acid 9.4 Synthesis of Optically Active Amino Acids from Asparagine/Glutamine 9.5 Syntheses from Other Amino Acids CHAPTER 10. SYNTHESIS OF OPTICALLY ACTIVE -AMINO ACIDS: ELABORATION OF SERINE 10.1 Introduction 10.2 Racemization of Serine 10.3 Nucleophilic Displacement of an Activated Serine Hydroxyl Group 10.4 Radical Reactions 10.5 Nucleophilic Alaninol Synthons Derived from Serine 10.6 Serine Aldehydes: Conversion of the Serine Carboxyl Group into an Aldehyde/Ketone 10.7 Serine Aldehydes: Conversion of the Serine Side Chain Hydroxyl Group into an Aldehyde 10.8 Other Reactions of Serine CHAPTER 11. SYNTHESIS OF -, -, -, AND -AMINO ACIDS 11.1 Introduction 11.2 b-Amino Acids 11.3 Cyclic b-Amino Acids 11.4 y-Amino Acids 11.5 Cyclic y-Amino Acids 11.6 -Amino Acids 11.7 Cyclic -Amino Acids 11.8 -Amino Acids CHAPTER 12. MODIFICATIONS OF AMINO ACIDS: RESOLUTION, N-ALKYLATION, N-PROTECTION, AMIDATION AND COUPLING 12.1 Resolutions of a-Amino Acids 12.2 N-Alkylation of Amino Acids 12.3 N-Acylation and N-Protection of Amino Acids 12.4 Amidation and Amide Hydrolysis 12.5 Coupling of Amino Acids