Superbases for Organic Synthesis

Preface

Acknowledgements

List of Contributors

1. General Aspects of Organosuperbases (Tsutomu Ishikawa)

2. Physicochemical Properties of Organic Superbases (Davor Margetic)

2.1 Introduction

2.2 Proton sponges

2.3 Amidines

2.4 Guanidines

2.5 Phosphazenes

2.6 Guanidinophosphazenes

2.7 Other Phosphorus Containing Superbases: Verkade's Proazaphosphatranes

2.8 Theoretical Methods

2.9 Concluding Remarks

References

3. Amidines in Organic Synthesis (Tsutomu Ishikawa and Takuya Kumamoto)

3.1 Introduction

3.2 Preparation of Amidine

3.3 Application of Amidines to Organic Synthesis

3.4 Amidinium Salt: Design and Synthesis

3.5 Concluding Remarks

References

4. Guanidines in Organic Synthesis (Tsutomu Ishikawa)

4.1. Introduction

4.2. Preparation of Chiral Guanidines

4.3 Guanidines as Synthetic Tools

4.4 Guanidinium Salt

4.5 Concluding Remarks

References

5. Phosphazene: Preparation, Reaction and Catalytic Role (Yoshinori Kondo)

5.1 Introduction

5.2 Deprotonative Transformations Using Stoichiometric Phosphazenes

5.3 Transformation Using Phosphazene Catalyst

5.4 Proazaphosphatrane Base (Verkade's Base)

5.5 Concluding Remarks

References

6. Polymer-supported Organosuperbases (Hiyoshizo Kotsuki)

6.1 Introduction

6.2 Acylation reactions

6.3 Alkylation Reactions

6.4 Heterocyclization

6.5 Miscellaneous

6.6 Concluding Remarks

References

7. Application of Organosuperbases to Total Synthesis (Kazuo Nagasawa)

7.1 Introduction

7.2 Carbon-carbon bond-forming reactions

7.3 Deprotection

7.4 Elimination

7.5 Ether synthesis

7.6 Heteroatom conjugate addition

7.7 Isomerization

7.8 Concluding Remarks

References

8. Related Organocatalysts (1): Proton Sponge (Kazuo Nagasawa)

8.1 Introduction

8.2 Alkylation and Hetero Michael reaction

8.3 Amide formation

8.4 Carbon-carbon bond-forming reaction

8.5 Palladium-catalyzed