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Summary
Summary
In this reference leaders at the forefront of research provide an insight into one of the hottest topics in organic synthesis, focusing on the most important enantioselective reactions.
Clearly structured, each entry begins with a concise introduction, including a mechanistic discussion of the reaction, followed by preparative guidelines for newcomers, such as carefully selected working procedures with critical notes for bench chemists, rules of thumb and tips and tricks.
Author Notes
Peter I. Dalko was born in 1960 in Budapest (Hungary). He studied chemistry at the Budapest TechnicalUniversity (Hungary) and obtained his doctorate with Dr. S. D. Géro in Gif-sur-Yvette (France). After undertaking postdoctoralresearch with Sir Derek H. Barton at Texas A&M University (USA) and Prof. Yoshito Kishi at Harvard University he joined Prof. Janine Cossy's research group at the ESPCI in Paris. His current main research interest is the development of novel asymmetric reactions.
Table of Contents
| Preface |
| List of Contributors |
| List of Abbreviations |
| 1 Asymmetric Organocatalysis: A New Stream in Organic SynthesisPeter I. Dalko |
| 1.1 Introduction |
| 1.2 Historical Background |
| 1.3 Catalysts |
| 1.4 Reaction Types |
| 1.5 How This Book is Organized |
| References and Notes |
| 2 Enamine Catalysis |
| 2.1 Aldol and Mannich-Type ReactionsFujie Tanaka and Carlos F. Barbas, III |
| 2.2 a-Heteroatom FunctionalizationMauro Marigo and Karl Anker J??rgensen |
| 2.3 Direct Conjugate Additions via Enamine ActivationCyril Bressy and Peter I. Dalko |
| 2.4 Conclusions |
| 3 Iminium CatalysisGerald Lelais and David W. C. MacMillan |
| 3.1 Introduction |
| 3.2 The Catalysis Concept of Iminium Activation |
| 3.3 Development of the "First-Generation" Imidazolidinone Catalysts |
| 3.4 Development of the "Second-Generation" Imidazolidinone Catalysts |
| 3.5 Cyloaddition Reactions |
| 3.6 1, 4-Addition Reactions |
| 3.7 Transfer Hydrogenation |
| 3.8 Organocatalytic Cascade Reactions |
| 3.9 Conclusions |
| 4 Ammonium Ions as Chiral TemplatesTakashi Ooi and Keiji Maruoka |
| 4.1 Introduction |
| 4.2 Homogeneous Catalysis with Chiral Quaternary Ammonium Fluorides |
| 4.3 Homogeneous Catalysis with Chiral Quaternary Ammonium Bifluorides |
| 4.4 Homogeneous Catalysis with Chiral Quaternary Ammonium Phenoxides |
| 4.5 Heterogeneous Catalysis: Chiral Phase-Transfer Catalysis |
| 4.6 Conclusions |
| 5 Organocatalytic Enantioselective Morita-Baylis-Hillman (MBH) ReactionsCandice Menozzi and Peter I. Dalko |
| 5.1 Addition of Ketones and Aldehydes to Activated Olefins |
| 5.2 Asymmetric Aza-MBH Reactions |
| 5.3 Conclusions |
| References and Notes |
| 6 Asymmetric Proton CatalysisJeff D. McGilvra and Vijaya Bhasker Gondi and Viresh H. Rawal |
| 6.1 Introduction |
| 6.2 Conjugate Addition Reactions |
| 6.3 Hydrocyanation Reactions |
| 6.4 Mannich Reactions |
| 6.5 Aza-Henry Reactions of Aldimines |
| 6.6 Acyl Pictet-Spengler Reactions of Iminium Ions |
| 6.7 Aza-Friedel-Crafts Reactions of Aldimines |
| 6.8 Hydrophosphonylation Reactions of Aldimines |
| 6.9 Direct Alkylation Reactions of I?-Diazoesters |
| 6.10 Imine Amidation Reactions |
| 6.11 Transfer Hydrogenation Reactions of Imines |
| 6.12 Morita-Baylis-Hillman Reactions |
| 6.13 Cycloaddition Reactions |
| 6.14 Aldol and Related Reactions |
| 6.15 Conclusion and Prospects |
| 6.16 Addendum |
| References |
| 7 Chiral Lewis Bases as CatalystsPavel Kocovsk?? and Andrei V. Malkov |
| 7.1 Introduction |
| 7.2 Allylation Reactions |
| 7.3 Propargylation, Allenylation, and Addition of Acetylenes |
| 7.4 Aldol-Type Reactions |
| 7.5 Hydrocyanation and Isonitrile Addition |
| 7.6 Reduction of Imines |
| 7.7 Epoxide Opening |
| 7.8 Conclusions and Outlook |
| 8 Asymmetric Acyl Transfer ReactionsAlan C. Spivey and Paul McDaid |
| 8.1 Introduction |
| 8.2 Type I Acyl Transfer Processes |
| 8.3 Type II Acyl Transfer Processes |
| 8.4 Concluding Remarks |
| 9 Nucleophilic N-Heterocyclic Carbenes in Asymmetric OrganocatalysisDieter Enders and Tim Balensiefer and Oliver Niemeier and Mathias Christmann |
| 9.1 The Benzoin Condensation |
| 9.2 The Stetter Reaction |
| 9.3 Further Applications |
| 10 Ylide-Based ReactionsEoghan M. McGarrigle and Varinder K. Aggarwal |
| 10.1 Introduction |
| 10.2 Epoxidation |
| 10.3 Asymmetric Aziridination |
| 10.4 Asymmetric Cyclopropanation |
| 10.5 Summary of Ylide-Catalyzed Asymmetric Reactions |
| 11 Organocatalytic Enantioselective Reduction of Olefins, Ketones, and Imines (H |
