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Book Details
Abstract
Due to the lower costs of nickel catalysts and the high abundance of nickel complexes, enantioselective nickel-mediated transformations have received a continuous and growing attention in recent years. This book demonstrates the diversity of chemistry catalysed by chiral nickel catalysts. Discussing several different enantioselective transformations, this book presents the impressive range of uses that have been found for novel and already known nickel chiral catalysts, from basic organic transformations to completely novel methodologies including fascinating one-pot domino and multicomponent reactions. This much-needed book is ideal for researchers and industrialists in organic chemistry, synthesis and medicinal chemistry.
Hélène Pellissier is a Researcher at CNRS, France. He research focusses on the chemistry of bisallylsilane and its large application in organic synthesis.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Enantioselective Nickel-Catalysed Transformations | i | ||
| Preface | vii | ||
| Abbreviations | xi | ||
| Contents | xv | ||
| Chapter 1 - Enantioselective Nickel-Catalysed Cycloaddition Reactions | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 1,3-Dipolar Cycloadditions | 1 | ||
| 1.3 Diels–Alder Cycloadditions | 20 | ||
| 1.4 Other Cycloadditions | 26 | ||
| 1.5 Conclusions | 30 | ||
| References | 32 | ||
| Chapter 2 - Enantioselective Nickel(ii)-Catalysed Conjugate Addition Reactions | 36 | ||
| 2.1 Introduction | 36 | ||
| 2.2 Conjugate Additions to Nitroalkenes | 39 | ||
| 2.2.1 1,3-Dicarbonyl Compounds as Nucleophiles | 39 | ||
| 2.2.1.1 Additions to Simple Nitroalkenes | 39 | ||
| 2.2.1.2 Additions to Other Nitroalkenes and Applications in Total Synthesis | 49 | ||
| 2.2.2 Other Nucleophiles | 52 | ||
| 2.3 Conjugate Additions to α,β-Unsaturated Carbonyl Compounds | 65 | ||
| 2.3.1 Additions to Enones | 65 | ||
| 2.3.2 Additions to α,β-Unsaturated Amides | 72 | ||
| 2.4 Conjugate Additions to Other Activated Alkenes | 76 | ||
| 2.5 Domino and Tandem Processes Initiated by a Michael Reaction | 79 | ||
| 2.6 Conclusions | 95 | ||
| References | 96 | ||
| Chapter 3 - Enantioselective Nickel-Catalysed Cross-Coupling Reactions | 103 | ||
| 3.1 Introduction | 103 | ||
| 3.2 Negishi Cross-Coupling Reactions | 104 | ||
| 3.3 Hiyama, Kumada, Suzuki, and Related Cross-Coupling Reactions | 118 | ||
| 3.4 Other Coupling Reactions | 128 | ||
| 3.5 Conclusions | 141 | ||
| References | 142 | ||
| Chapter 4 - Enantioselective Nickel-Catalysed Domino and Tandem Reactions | 146 | ||
| 4.1 Introduction | 146 | ||
| 4.2 Two-Component Domino Reactions | 147 | ||
| 4.2.1 Domino Reactions Initiated by the Michael Reaction | 147 | ||
| 4.2.2 Miscellaneous Domino Reactions | 158 | ||
| 4.3 Multicomponent Reactions | 173 | ||
| 4.3.1 Three-Component Couplings of Unsaturated Hydrocarbons, Carbonyl Compounds and Derivatives, and Reducing Agents | 174 | ||
| 4.3.1.1 Reactions of 1,3-Dienes, Carbonyl Compounds, and Reducing Agents | 174 | ||
| 4.3.1.2 Reactions of Allenes, Aldehydes, and Reducing Agents | 182 | ||
| 4.3.1.3 Reactions of Alkynes, Aldehydes or Aldimines, and Reducing Agents | 184 | ||
| 4.3.2 Miscellaneous Multicomponent Reactions | 190 | ||
| 4.4 Tandem Sequences | 195 | ||
| 4.5 Conclusions | 198 | ||
| References | 201 | ||
| Chapter 5 - Enantioselective Nickel-Catalysed Hydrovinylation, Hydrophosphination, Hydrocyanation, and Hydroalkynylation Reactions of Alkenes | 206 | ||
| 5.2 Hydrovinylations | 207 | ||
| 5.3 Hydrophosphinations | 219 | ||
| 5.4 Hydrocyanations | 221 | ||
| 5.5 Hydroalkynylations | 224 | ||
| 5.6 Conclusions | 227 | ||
| References | 228 | ||
| Chapter 6 - Enantioselective Nickel-Catalysed α-Heterofunctionalisation, and α-Arylation/Alkylation Reactions of Carbonyl Compounds | 232 | ||
| 6.1 Introduction | 232 | ||
| 6.2 α-Halogenations | 233 | ||
| 6.3 α-Aminations | 243 | ||
| 6.4 α-Hydroxylations | 249 | ||
| 6.5 α-Arylations and α-Alkylations | 250 | ||
| 6.6 Conclusions | 256 | ||
| References | 257 | ||
| Chapter 7 - Enantioselective Nickel-Catalysed Additions of Organometallic Reagents to Aldehydes | 261 | ||
| 7.1 Introduction | 261 | ||
| 7.2 Additions of Organoaluminum Reagents | 261 | ||
| 7.3 Additions of Organozinc Reagents | 267 | ||
| 7.4 Additions of Organoboron Reagents | 273 | ||
| 7.5 Conclusions | 276 | ||
| References | 276 | ||
| Chapter 8 - Enantioselective Nickel-Catalysed Aldol-Type and Mannich-Type Reactions | 279 | ||
| 8.1 Introduction | 279 | ||
| 8.2 Aldol-Type Reactions | 280 | ||
| 8.3 Mannich-Type Reactions | 288 | ||
| 8.4 Conclusions | 294 | ||
| References | 295 | ||
| Chapter 9 - Enantioselective Nickel-Catalysed Hydrogenation Reactions | 299 | ||
| 9.1 Introduction | 299 | ||
| 9.2 Hydrogenations of Ketones | 300 | ||
| 9.3 Hydrogenations of Alkenes | 305 | ||
| 9.4 Conclusions | 306 | ||
| References | 307 | ||
| Chapter 10 - Enantioselective Nickel-Catalysed Miscellaneous Reactions | 310 | ||
| 10.1 Introduction | 310 | ||
| 10.2 Cyclisation Reactions | 310 | ||
| 10.3 Amination Reactions | 317 | ||
| 10.4 Ring-Opening Reactions | 319 | ||
| 10.5 Friedel–Crafts Reactions | 323 | ||
| 10.6 Allylation Reactions of Aldehydes | 325 | ||
| 10.7 Other Reactions | 328 | ||
| 10.8 Conclusions | 339 | ||
| References | 339 | ||
| Chapter 11 - General Conclusions | 343 | ||
| References | 358 | ||
| Subject Index | 359 |