New Frontiers in Asymmetric Catalysis

Abstract

PREFACE. CONTRIBUTORS. 1 Ligand Design for Catalytic Asymmetric Reduction (Takeshi Ohkuma, Masato Kitamura, and Ryoji Noyori) 1.1 Introduction. 1.2 Hydrogenation of Olefins. 1.3 Reduction of Ketones. 1.4 Reduction of Imines. References. 2 Ligand Design for Oxidation (Tohru Yamada) 2.1 Introduction. 2.2 Catalytic Enantioselective Epoxidation of Unfunctionalized Olefins. 2.3 Enantioselective Metal-Catalyzed Baeyer-Villiger Oxidation. 2.4 Optical Resolution during Oxidation of Alcohols. 2.5 Catalytic Enantioselective Oxidative Coupling of 2-Naphthols. 2.6 Concluding Remarks. References. 3 Ligand Design for C-C Bond Formation (Ryo Shintani and Tamio Hayashi). 3.1 Introduction. 3.2 1,4-Addition and Related Reactions. 3.3 Cross-Coupling Reactions. References. 4 Activation of Small Molecules (CO, HCN, RNC, and CO2) (Kyoko Nozaki). 4.1 Introduction. 4.2 Asymmetric Hydroformylation of Olefins. 4.3 Asymmetric Hydrocarbohydroxylation and Related Reactions. 4.4 Asymmetric Ketone Formation from Carbon-Carbon Multiple Bonds and CO. 4.5 Asymmetric Hydrocyanation of Olefins. 4.6 Asymmetric Addition of Cyanide and Isocyanide to Aldehydes or Imines. 4.7 Asymmetric Addition of Carbon Dioxide. 4.8 Conclusion and Outlook. References. 5 Asymmetric Synthesis Based on Catalytic Activation of CH Bonds and CC Bonds (Zhiping Li and Chao-Jun Li) 5.1 Introduction. 5.2 Asymmetric Synthesis via Activation of C-H Bonds. 5.3 Asymmetric Synthesis via Activation of C-C Bonds. 5.4 Conclusions and Outlook. Acknowledgments. References. 6 Recent Progress in the Metathesis Reaction (Miwako Mori). 6.1 Introduction. 6.2 Olefin Metathesis. 6.3 Enyne Metathesis. 6.4 Alkyne Metathesis. 6.5 Conclusions. References. 7 Nonlinear Effects in Asymmetric Catalysis (Henri B. Kagan) 7.1 Introduction. 7.2 Properties of Enantiomer Mixtures. 7.3 Nonlinear Effect in Asymmetric Catalysis. 7.4 Main Classes of Reactions. 7.5 Asymmetric Amplification. 7.6 Current Trends. 7.7 Conclusion. Acknowledgment. References and Notes. 8 Asymmetric Activation and Deactivation of Racemic Catalysts (Koichi Mikami and Kohsuke Aikawa). 8.1 Introduction. 8.2 Racemic Catalysis. 8.2.1 Asymmetric Deactivation. 8.3 Future Perspectives. References and Notes. 9 Asymmetric Autocatalysis with Amplification of Chirality and Origin of Chiral Homogeneity of Biomolecules (Kenso Soai, Tsuneomi Kawasaki, and Itaru Sato). 9.1 Introduction. 9.2 Asymmetric Autocatalysis. 9.3 Amplification of Chirality by Asymmetric Autocatalysis. 9.4 Asymmetric Autocatalysis and Its Role in the Origin and Amplification of Chirality. 9.5 Conclusions. Acknowledgment. References. 10 Recent Advances in Catalytic Asymmetric Desymmetrization Reactions (Tomislav Rovis). 10.1 Introduction. 10.2 Allylic Alkylation. 10.3 Ring Opening of Epoxides and Aziridines. 10.4 Ring Opening of Bridged Systems. 10.5 Olefin Metathesis. 10.6 Acylation. 10.7 Asymmetric Deprotonation. 10.8 Oxidations. 10.9 Cyclic Anhydride Desymmetrization. 10.10 Miscellaneous. 10.11 Concluding Remarks. Acknowledgments. References. 11 History and Perspective of Chiral Organic Catalysts (Gerald Lelais and David W. C. MacMillan). 11.1 Introduction. 11.2 Historical Background. 11.3 Iminium Catalysis: A New Concept in Organocatalysis. 11.4 Enamine Catalysis: Birth, Rebirth, and Rapid Growth. 11.5 Bronsted Acid Catalysis: Hydrogen-Bonding Activation. 11.6 Phase Transfer Catalysis (PTC). 11.7 Future Perspective. Acknowledgments. References and Notes. 12 Chiral Bronsted/Lewis Acid Catalysts (Kazuaki Ishihara and Hisashi Yamamoto). 12.1 Introduction. 12.2 Chiral Bronsted Acid Catalysts. 12.3 Chiral Lewis Acid Catalysts. 12.4 Lewis Acid--Assisted Chiral Bronsted Acid Catalysts. 12.5 Conclusions and Outlook. References. 13 Chiral Bifunctional Acid/Base Catalysts (Masakatsu Shibasaki and Motomu Kanai) 13.1 Introduction. 13.2 Chiral Bro nsted Base Catalysis. 13.3 Chiral Bronsted Base--Lewis Acid Bifunctional Catalysis. 13.4 Chiral Bronsted Base--Bronsted Acid Bifunctional Catalysis. 13.5 Chiral Lewis Base Catalysis. 13.6 Chiral Lewis Base--Lewis Acid Bifunctional Catalysis. 13.7 Conclusion. References and Notes. Index.