Asymmetric Synthesis of 3,3-Disubstituted Oxindoles

The following sections are included:

• Preface
• About the Authors
• Contents

Oxindole (indolin-2-one) chemistry began to develop with the study of the dye indigo, which was easily converted to isatin and then to oxindole. When in 1866, Adolf von Baeyer reduced oxindole to indole, it was then able to propose its chemical formula [1]. It is an aromatic heterocyclic organic compound with a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring (indoline skeleton) substituted with a carbonyl group at the second position of the five-member ring (Figure 1.1). After their discovery, indole derivatives were prepared as important dyestuffs in analogy with indigo, and only since the 1930s, interest in indole was intensified as it became clear that indole skeleton was present in many important alkaloids. Now, the indole ring is recognized as the most common heterocycle present in nature [2]. For this reason, substituted indoles have been referred to as “privileged structures” and a number of approved drugs as well as natural products belong to this family. This biological activity and structural complexity have stimulated generations of synthetic chemists to design strategies for assembling these structures and this field of chemistry is growing drastically…

The following sections are included:

• Introduction
• Organometallic Approaches
• Organocatalytic Approaches
• Synergistic Methodologies for the Synthesis of Spirooxindoles
• Conclusions
• References

The following sections are included:

• Introduction
• de novo Construction
• Nucleophilic Substitution Reactions
• Aldol Reactions
• Mannich Reactions
• Michael Reactions
• Rearrangements
• Desymmetrization
• Appendix A. Catalysts Cited in This Chapter
• Appendix B. List of Abbreviation
• Appendix C. Natural Products Cited in This Chapter
• References

The following sections are included:

• Introduction
• Nucleophilic Additions to Isatin Imines
• Domino and Tandem Reactions
• Direct Aminations of 3-Substituted Oxindoles
• Miscellaneous Reactions
• Conclusions
• Appendix A. Catalysts Cited in This Chapter
• Appendix B. List of Abbreviation
• References

The following sections are included:

• Introduction
• Asymmetric Aldol Reaction of Isatins
• Asymmetric Henry Reaction of Isatins
• Asymmetric Arylation Reaction of Isatins
• Asymmetric Friedel–Crafts Reaction of Isatins
• Asymmetric Hydrophosphonylation Reaction of Isatins
• Asymmetric Morita–Baylis–Hillman Reaction
• Asymmetric Michael Reaction of Isatin
• Decarboxylative Addition to Isatins
• Hydroxylation Reaction
• Addition of Organotrimethoxysilanes to Isatins
• Hetero-ene Reaction
• Allylation, Crotylation and Prenylation of Isatins
• Anilide Cyclizations
• Appendix A. Catalysts and Ligands Cited in this Chapter
• Appendix B. List of Abbreviation
• References

The following sections are included:

• Introduction
• 3-Fluoro-3-Substituted Oxindoles
• Other Halogens
• Sulfur
• Phosphorus
• Appendix A. Catalysts Cited in this Chapter
• Appendix B. List of Abbreviation
• Appendix C. Natural Products Cited in this Chapter
• References

The following section is included:

• Index