Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts

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 reaction.

8.6 Concluding Remarks.

References.

9. Related Organocatalysts (2): Urea Derivatives (Waka Nakanishi).

9.1 Introduction.

9.2 Bisphenol as Organoacid Catalyst.

9.3 Urea and Thiourea as Achiral Catalysts.

9.4 Urea and Thiourea as Chiral Catalyst.

9.5 Concluding Remarks.

References.

10. Amidines and Guanidines in Natural Products and Medicines (Takuya Kumamoto).

10.1 Introduction.

10.2 Natural Amidine Derivatives.

10.3 Natural Guanidine Derivatives.

10.4 Medicinal Amidine and Guanidine Derivatives.

References.

11. Perspective (Tsutomu Ishikawa and Davor Margetic).