Covering all of the literature since the beginning of 2006, this must-have book for chemists collects the major progress in the field of enantioselective one-, two-, and multicomponent domino reactions promoted by chiral metal catalysts. It clearly illustrates how enantioselective metal-catalyzed processes constitute outstanding tools for the development of a wide variety of fascinating one-pot asymmetric domino reactions, thereby allowing many complex products to be easily generated from simple materials in one step. The book also strictly follows the definition of domino reactions by Tietze as single-, two-, as well as multicomponent transformations.
Asymmetric Metal Catalysis in Enantioselective Domino Reactions is divided into twelve chapters, dealing with enantioselective copper-, palladium-, rhodium-, scandium-, silver-, nickel-, gold-, magnesium-, cobalt-, zinc-, yttrium and ytterbium-, and other metal-catalyzed domino reactions. Most of the chapters are divided into two parts dealing successively with one- and two-component domino reactions, and three-component processes. Each part is subdivided according to the nature of domino reactions. Each chapter of the book includes selected applications of synthetic methodologies to prepare natural and biologically active products.
-Presents the novel combination of asymmetric metal catalysis with the concept of fascinating domino reactions, which allows high molecular complexity with a remarkable level of enantioselectivity
-Showcases an incredible tool synthesizing complex and diverse chiral structures in a single reaction step
-Includes applications in total synthesis of natural products and biologically active compounds
-Written by a renowned international specialist in the field
-Stimulates the design of novel asymmetric domino reactions and their use in the synthesis of natural products, pharmaceuticals, agrochemicals, and materials
Asymmetric Metal Catalysis in Enantioselective Domino Reactions will be of high interest to synthetic, organic, medicinal, and catalytic chemists in academia and R&D departments.
Table of Contents
Preface ix
List of Abbreviations xiii
About the Author xvii
1 Enantioselective Copper-Catalyzed Domino Reactions 1
1.1 Introduction 1
1.2 Two-Component Processes 2
1.2.1 Reactions Based on Cyclizations 2
1.2.2 Reactions Initiated by Michael Additions 9
1.2.3 Reactions Initiated by Friedel-Crafts Reactions 15
1.2.4 Reactions Initiated by Aldol Reactions 16
1.2.5 Miscellaneous Reactions 19
1.3 Three-Component Processes 23
1.3.1 Reactions Based on Alkyne Couplings 23
1.3.1.1 Reactions of Alkynes, Aldehydes, and Amines 23
1.3.1.2 Other Alkyne Couplings 33
1.3.2 Reactions Initiated by Michael Additions 34
1.3.3 Reactions Based on 1,3-Dipolar Cycloadditions 41
1.3.4 Reactions Based on Addition Reactions to Alkenes 45
1.3.5 Reactions Based on Alkene Couplings 48
1.3.6 Miscellaneous Reactions 50
1.4 Conclusions 50
References 51
2 Enantioselective Palladium-Catalyzed Domino Reactions 57
2.1 Introduction 57
2.2 One- and Two-Component Processes 57
2.2.1 Reactions Based on Heck Reactions 57
2.2.2 Reactions Initiated by Wacker Reactions 65
2.2.3 Reactions Based on Cyclizations 68
2.2.4 Reactions Initiated by Michael Additions 74
2.2.5 Miscellaneous Reactions 77
2.3 Three-Component Processes 80
2.3.1 Reactions Based on Alkene Couplings 80
2.3.2 Three-Component Reactions Initiated by Wacker Reactions 82
2.3.3 Miscellaneous Reactions 86
2.4 Conclusions 91
References 91
3 Enantioselective Rhodium-Catalyzed Domino Reactions 95
3.1 Introduction 95
3.2 One- and Two-Component Processes 95
3.2.1 Reactions Based on [2+2+2] Cycloadditions 95
3.2.2 Reactions Based on 1,3-Dipolar Cycloadditions 100
3.2.3 Reactions Initiated by Ring-Opening Reactions 105
3.2.4 Reactions Initiated by Michael Additions 105
3.2.5 Reactions Based on Cyclizations 107
3.2.6 Miscellaneous Reactions 113
3.3 Three-Component Processes 115
3.3.1 Reactions Based on Alkyne Couplings 115
3.3.2 Reactions Initiated by Cycloadditions 118
3.3.3 Miscellaneous Reactions 121
3.4 Conclusions 124
References 124
4 Enantioselective Scandium-Catalyzed Domino Reactions 129
4.1 Introduction 129
4.2 One- and Two-Component Processes 130
4.2.1 Domino Bromination/Aminocyclization Reactions 130
4.2.2 Reactions Initiated by Ring-Opening Reactions 134
4.2.3 Reactions Initiated by Michael Additions 136
4.2.4 Domino Diazoalkane Addition/1,2-Rearrangement Reactions 139
4.2.5 Domino Imine Formation/Intramolecular Amidation Reactions 143
4.2.6 Miscellaneous Reactions 145
4.3 Three-Component Processes 153
4.3.1 Reactions Based on Mannich Couplings 153
4.3.2 Miscellaneous Reactions 155
4.4 Conclusions 162
References 163
5 Enantioselective Silver-Catalyzed Domino Reactions 167
5.1 Introduction 167
5.2 One- and Two-Component Processes 168
5.2.1 Reactions Initiated by Michael Additions 168
5.2.2 Reactions Based on Cyclizations 186
5.2.3 Reactions Initiated by Aldol Reactions 193
5.2.4 Domino Reactions Initiated by Mannich Reactions 197
5.2.5 Miscellaneous Reactions 200
5.3 Three-Component Processes 204
5.3.1 Reactions Based on Mannich Reactions 204
5.3.2 Reactions Based on 1,3-Dipolar Cycloadditions 205
5.3.3 Miscellaneous Reactions 207
5.4 Conclusions 208
References 209
6 Enantioselective Nickel-Catalyzed Domino Reactions 213
6.1 Introduction 213
6.2 Two-Component Processes 213
6.2.1 Reactions Initiated by Michael Additions 213
6.2.2 Reactions Based on Cyclizations 221
6.2.3 Miscellaneous Reactions 226
6.3 Three-Component Processes 235
6.3.1 Reactions Based on Alkene Couplings 235
6.3.2 Reactions Based on Alkyne Couplings 238
6.3.3 Miscellaneous Reactions 241
6.4 Conclusions 244
References 245
7 Enantioselective Gold-Catalyzed Domino Reactions 249
7.1 Introduction 249
7.2 One- and Two-Component Processes Based on Cyclizations 249
7.2.1 Reactions of 1,6-Enynes 249
7.2.2 Other Reactions 254
7.3 Three-Component Processes Based on Alkyne Couplings 263
7.4 Conclusions 266
References 266
8 Enantioselective Magnesium-Catalyzed Domino Reactions 269
8.1 Introduction 269
8.2 Two-Component Domino Reactions Initiated by Michael Additions 269
8.3 Miscellaneous One- and Two-Component Domino Reactions 274
8.4 Multicatalyzed Reactions 283
8.5 Conclusions 288
References 290
9 Enantioselective Cobalt-Catalyzed Domino Reactions 293
9.1 Introduction 293
9.2 One- and Two-Component Processes 293
9.3 Three-Component Processes 300
9.4 Conclusions 301
References 302
10 Enantioselective Zinc-Catalyzed Domino Reactions 305
10.1 Introduction 305
10.2 Two-Component Processes Initiated by Michael Additions 305
10.3 Three-Component Processes 311
10.4 Conclusions 314
References 314
11 Enantioselective Yttrium- and Ytterbium-Catalyzed Domino Reactions 317
11.1 Introduction 317
11.2 Two-Component Processes 318
11.2.1 Reactions Initiated by Aldol Additions 318
11.2.2 Miscellaneous Reactions 321
11.3 Three-Component Processes 324
11.3.1 Three-Component Processes Based on Cycloadditions 324
11.3.2 Miscellaneous Reactions 327
11.4 Conclusions 330
References 331
12 Enantioselective Domino Reactions Catalyzed by Other Metals 333
12.1 Introduction 333
12.2 One- and Two-Component Processes 333
12.2.1 Iron-Catalyzed Reactions 333
12.2.2 Zirconium-Catalyzed Reactions 337
12.2.3 Platinum-Catalyzed Reactions 339
12.2.4 Iridium-Catalyzed Reactions 343
12.2.5 Aluminum-Catalyzed Reactions 344
12.2.6 Tin-Catalyzed Reactions 345
12.2.7 Ruthenium-Catalyzed Reactions 348
12.2.8 Titanium-Catalyzed Reactions 349
12.2.9 Vanadium-Catalyzed Reactions 352
12.2.10 Gallium-Catalyzed Reactions 353
12.3 Three-Component Processes 355
12.3.1 Iridium-Catalyzed Reactions 355
12.3.2 Boron-Catalyzed Reactions 358
12.3.3 Aluminum-Catalyzed Reactions 360
12.3.4 Tin-Catalyzed Reactions 361
12.3.5 Zirconium-Catalyzed Reactions 362
12.4 Conclusions 363
References 365
Index 369
