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Index
Cover
Related Titles
Title Page
Copyright
List of Contributors
Introduction
Chapter 1: The Primary Organometallic in Copper-Catalyzed Reactions
1.1 Scope and Introduction
1.2 Terminal Organometallics Sources Available
1.3 Coordination Motifs in Asymmetric Copper Chemistry
1.4 Asymmetric Organolithium–Copper Reagents
1.5 Asymmetric Grignard–Copper Reagents
1.6 Asymmetric Organozinc–Copper Reagents
1.7 Asymmetric Organoboron–Copper Reagents
1.8 Asymmetric Organoaluminium–Copper Reagents
1.9 Asymmetric Silane and Stannane Copper-Promoted Reagents
1.10 Conclusions
References
Chapter 2: Copper-Catalyzed Asymmetric Conjugate Addition
2.1 Introduction
2.2 Conjugate Addition
2.3 Trapping of Enolates
References
Chapter 3: Copper-Catalyzed Asymmetric Conjugate Addition and Allylic Substitution of Organometallic Reagents to Extended Multiple-Bond Systems
3.1 Introduction
3.2 Copper-Catalyzed Asymmetric Conjugate Addition (ACA) to Polyconjugated Michael Acceptors
3.3 Copper-Catalyzed Asymmetric Allylic Substitution on Extended Multiple-Bond Systems
3.4 Conclusion
References
Chapter 4: Asymmetric Allylic Alkylation
4.1 Introduction
4.2 Nucleophiles in Enantioselective Process Development
4.3 Functionalized Substrates
4.4 Desymmetrization of meso-Allylic Substrates
4.5 Kinetic Resolution Processes
4.6 Direct Enantioconvergent Transformation
4.7 Conclusion and Perspectives
References
Chapter 5: Ring Opening of Epoxides and Related Systems
5.1 Introduction
5.2 Copper-Catalyzed Asymmetric Ring Opening of Epoxides with Amines
5.3 Copper-Catalyzed Asymmetric Ring Opening of Epoxides and Aziridines with Organometallic Reagents
5.4 Copper-Catalyzed Asymmetric Ring Opening of Heterobicyclic Systems with Organometallic Reagents
5.5 Conclusions
References
Chapter 6: Carbon–Boron and Carbon–Silicon Bond Formation
6.1 Introduction
6.2 C–B Bond Formation Reactions
6.3 C–Si Bond Formation Reactions
6.4 Summary
References
Chapter 7: CuH in Asymmetric Reductions
7.1 Introduction
7.2 Asymmetric Conjugate Reductions
7.3 Asymmetric 1,2-Additions
7.4 Heterogeneous Catalysis
7.5 Conclusions and Perspective
References
Chapter 8: Asymmetric Cyclopropanation and Aziridination Reactions
8.1 Introduction
8.2 Asymmetric Cyclopropanation
8.3 Asymmetric Aziridination
8.4 Conclusion
References
Chapter 9: Copper-Catalyzed Asymmetric Addition Reaction of Imines
9.1 Introduction
9.2 Copper-Catalyzed Asymmetric Addition Reaction of Dialkylzinc to Imines
9.3 Copper-Catalyzed Asymmetric Allylation, Arylation, and Alkynylation Reactions of Imines
9.4 Copper as a Lewis Acid Catalyst for Asymmetric Reaction of Imines
9.5 Conclusions
References
Chapter 10: Carbometallation Reactions
10.1 Introduction
10.2 Carbometallation of Cyclopropenes
10.3 Carbometallation of Alkynes
10.4 Summary
Acknowledgments
References
Chapter 11: Chiral Copper Lewis Acids in Asymmetric Transformations
11.1 Introduction
11.2 Cycloadditions
11.3 Claisen Rearrangements
11.4 Ene Reactions
11.5 Nucleophilic Addition to C=O and C=N Double Bonds
11.6 Conjugate Additions
11.7 α-Functionalization of Carbonyl Compounds
11.8 Kinetic Resolution
11.9 Asymmetric Desymmetrization
11.10 Free-Radical Reactions
11.11 Conclusions
References
Chapter 12: Mechanistic Aspects of Copper-Catalyzed Reactions
12.1 Introduction
12.2 Conjugate Addition
12.3 Allylic Alkylation and Substitution
12.4 Copper as Lewis Acid
12.5 1,2-Addition to Imines and Carbonyls
12.6 Copper Hydride
12.7 Cyclopropanation, Aziridination, and Allylic Oxidation
References
Chapter 13: NMR Spectroscopic Aspects
13.1 Introduction
13.2 Copper Complexes with Phosphoramidite Ligands
13.3 Copper Complexes with TADDOL-Based Thiolate Ligands
13.4 Copper Complexes with Ferrocenyl-Based Ligands
13.5 Conclusion
Acknowledgment
References
Chapter 14: Applications to the Synthesis of Natural Products
14.1 Introduction
14.2 Copper-Catalyzed Conjugate Additions in Natural Product Synthesis
14.3 Natural Product Synthesis Employing Asymmetric Allylic Alkylation
14.4 Asymmetric Copper-Catalyzed Diels–Alder Reactions
14.5 Asymmetric Copper-Catalyzed Mukaiyama Aldol Reactions
14.6 Other Asymmetric Copper-Catalyzed Aldol-Type Reactions
14.7 Asymmetric 1,3-Dipolar Cycloaddition and Claisen Rearrangement
14.8 Catalytic Asymmetric Cyclopropanation
14.9 Asymmetric Copper-Catalyzed Conjugate Reductions
14.10 Copper-Catalyzed Asymmetric 1,2-Type Addition Reactions
14.11 Miscellaneous Asymmetric Copper-Catalyzed Reactions
14.12 Conclusion
References
Index
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