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Domino Reactions: Concepts for Efficient Organic Synthesis

Lutz F. Tietze (Editor)
ISBN: 978-3-527-33432-2
648 pages
March 2014
Domino Reactions: Concepts for Efficient Organic Synthesis (3527334327) cover image

The follow-up to the successful "Domino Reaction in Organic Synthesis", this ready reference brings up to date on the original concept. The chapters have been arranged according to the name of well-known transformations of the first step and in combination with the formed products. Each chapter is written by an internationally renowned expert, and the book is edited by L. F. Tietze, who established the concept of domino reactions.

The one-stop source for all synthetic chemists to improve the synthetic efficiency and allow an ecologically and economically beneficial preparation of every chemical compound.

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Preface XIII

List of Contributors XV

List of Abbreviations XIX

Introduction 1

References 4

1 Transition-Metal-Catalyzed Carbonylative Domino Reactions 7
Xiao-Feng Wu, Helfried Neumann, and Matthias Beller

1.1 Introduction 7

1.2 Transition-Metal-Catalyzed Carbonylative Domino Reactions 8

1.2.1 Ruthenium-Catalyzed Carbonylative Domino Reactions 8

1.2.2 Rhodium-Catalyzed Carbonylative Domino Reactions 13

1.2.3 Palladium-Catalyzed Carbonylative Domino Reactions 16

1.2.4 Iron-, Copper-, Nickel-, and Cobalt-Catalyzed Carbonylative Domino Reactions 24

1.3 Outlook 27

References 27

2 Metathesis Reactions in Domino Processes 31
Kamal M. Dawood and Peter Metz

2.1 Domino Processes Featuring Solely Metathesis Events 31

2.1.1 Reactions Involving Only Alkenes 31

2.1.2 Reactions Involving Alkenes and Alkynes 41

2.2 Domino Processes Featuring Metathesis and Non-metathesis Events 52

2.2.1 Metathesis/Redox Transformation 52

2.2.2 Metathesis/Isomerization 53

2.2.3 Metathesis/Cycloaddition 56

2.2.4 Metathesis/Substitution 58

2.2.5 Metathesis/Conjugate Addition 59

2.2.6 Metathesis/Carbonyl Olefination 62

2.3 Conclusion and Outlook 63

Acknowledgments 63

References 63

3 C–H Activation Reactions in Domino Processes 67
Gavin Chit Tsui and Mark Lautens

3.1 Heck Reactions/C–H Activations 67

3.2 Carbopalladations and Aminopalladations of Alkynes/C–H Activations 72

3.3 Palladium-Catalyzed/Norbornene-Mediated ortho C–H Activations 80

3.4 Domino Reactions Involving Heteroatom-Directed C–H Activations 96

3.5 Conclusions 101

References 101

4 Domino Reactions Initiated by Nucleophilic Substitution 105
Hiriyakkanavar Ila, Anand Acharya, and Saravanan Peruncheralathan

4.1 Domino SN/Michael Addition and Related Reactions 106

4.2 Domino Reactions Initiated by Nucleophilic Ring Opening of Aziridines, Epoxides, and Activated Cyclopropanes 115

4.3 Domino SN/Brook Rearrangements 127

References 138

5 Radical Reactions in Domino Processes 141
Guanghui An and Guigen Li

5.1 Introduction 141

5.2 Radical/Cation Domino Processes 143

5.3 Radical/Anionic Domino Processes 148

5.4 Domino Radical/Radical Process 154

5.5 Radical/Pericyclic Domino Processes 172

5.6 Asymmetric Radical Domino Processes 174

5.6.1 Chiral Auxiliary-Directed Asymmetric Radical Domino Processes 174

5.6.2 Chiral Catalyst-Driven Asymmetric Radical Domino Processes 176

5.7 Conclusion and Outlook 178

Acknowledgments 179

References 179

6 Pericyclic Reactions in Domino Processes 183
Lukas J. Patalag and Daniel B. Werz

6.1 Introduction 183

6.2 Cycloadditions 184

6.2.1 Cycloaddition/Cycloaddition 184

6.2.2 Cycloaddition/Cycloreversion 185

6.2.3 Cycloaddition/Sigmatropic Rearrangement 188

6.2.4 Cycloaddition/Electrocyclization 189

6.2.5 Cycloaddition/Mixed Transformations 191

6.3 Sigmatropic Rearrangements 192

6.3.1 Sigmatropic Rearrangement/Sigmatropic Rearrangement 192

6.3.2 Sigmatropic Rearrangement/Cycloaddition 195

6.3.3 Sigmatropic Rearrangement/Electrocyclization 196

6.3.4 Sigmatropic Rearrangement/Mixed Transformations 199

6.4 Electrocyclizations 201

6.4.1 Electrocyclization/Electrocyclization 201

6.4.2 Electrocyclization/Cycloaddition 202

6.4.3 Electrocyclization/Sigmatropic Rearrangement 205

6.4.4 Electrocyclization/Mixed Transformations 208

6.5 Mixed Transformations 209

6.5.1 Mixed Transformations Followed by Pericyclic Reactions 209

6.5.2 Cascades of Carbopalladations Followed by Pericyclic Reactions 211

6.5.3 Domino Knoevenagel/Hetero Diels–Alder Reaction 214

6.6 Concluding Remarks 214

Acknowledgments 215

References 215

7 Modern Domino Reactions Containing a Michael Addition Reaction 219
Scott G. Stewart

7.1 Introduction 219

7.2 Formation of Acyclic Products 221

7.3 Formation of Carbocycles 225

7.4 Formation of O-Heterocycles 236

7.5 Formation of N-Heterocycles 250

7.6 Formation of S-Heterocycles 257

7.7 Formation of Heterocycles Containing Nitrogen and Oxygen 260

References 262

8 Aldol Reactions in Domino Processes 267
Christoph Schneider and Michael Boomhoff

8.1 Introduction 267

8.2 Domino Processes with the Aldol Reaction as First Step 267

8.2.1 Aldol-Lactonization Reactions 267

8.2.2 Aldol/Prins Reactions 270

8.2.3 Aldol/Acetalization Reactions 272

8.2.4 Aldol–Tishchenko Reactions 273

8.2.5 Vinylogous Aldol/Michael Reactions 276

8.3 Domino Processes with the Aldol Reaction as Subsequent Step 277

8.3.1 Conjugate Addition/Aldol Reactions 277

8.3.1.1 Addition of Carbon Nucleophiles 277

8.3.1.2 Addition of Sulfur Nucleophiles 281

8.3.1.3 Addition of Oxygen and Nitrogen Nucleophiles 283

8.3.1.4 Iodo-Aldol Reactions 285

8.3.1.5 Reductive Aldol Reactions 287

8.3.2 Isomerization/Aldol Reactions 289

8.3.3 Wittig Rearrangement/Aldol Reactions 290

8.3.4 Cycloaddition/Aldol Reactions 290

8.4 Conclusion and Outlook 292

References 292

9 Oxidations and Reductions in Domino Processes 295
Govindasamy Sekar, Iyyanar Karthikeyan, and Dhandapani Ganapathy

9.1 Introduction 295

9.2 Domino Reactions Initiated by Oxidation or Reduction Reaction 296

9.2.1 Domino Reactions Initiated by an Oxidation Reaction 296

9.2.2 Domino Reactions Initiated by Reduction Reaction 301

9.3 Domino Reactions Having Oxidation in Middle of the Sequence 312

9.4 Domino Reactions Terminated by Oxidation or Reduction Reaction 313

9.4.1 Domino Reactions Terminated by Oxidation Reaction 313

9.4.2 Domino Reactions Terminated by Reduction Reaction 314

9.5 Conclusion 319

Acknowledgments 319

References 319

10 Organocatalysis in Domino Processes 325
H´el`ene Pellissier

10.1 Introduction 325

10.2 One- and Two-Component Domino Reactions 326

10.2.1 Domino Reactions Initiated by the Michael Reaction 327

10.2.1.1 Domino Michael/Michael Reactions 327

10.2.1.2 Domino Michael/Aldol Reactions 334

10.2.1.3 Domino Michael/Intramolecular Heterocyclization Reactions 340

10.2.1.4 Domino Michael/Intramolecular Alkylation Reactions 349

10.2.1.5 Domino Michael/(aza)–Henry Reactions 352

10.2.1.6 Domino Michael/Knoevenagel Reactions 355

10.2.1.7 Domino Michael/aza-Morita–Baylis–Hillman Reactions 357

10.2.1.8 Domino Michael/Mannich Reactions 357

10.2.1.9 Other Domino Reactions Initiated by the Michael Reaction 359

10.2.2 Domino Reactions Initiated by Other Reactions 361

10.2.2.1 Domino Reactions Initiated by the Indirect Mannich Reaction 361

10.2.2.2 Domino Reactions Initiated by the (Aza)-Morita–Baylis–Hillman Reaction 363

10.2.2.3 Domino Reactions Initiated by the Friedel–Crafts Reaction 364

10.2.2.4 Miscellaneous Domino Reactions 365

10.3 Multicomponent Reactions 371

10.3.1 Multicomponent Reactions Initiated by the Michael Reaction 371

10.3.1.1 Michael Reactions of α,β-Unsaturated Aldehydes 371

10.3.1.2 Michael Reactions of Other α,β-Unsaturated Carbonyl Compounds 378

10.3.1.3 Michael Reactions of Nitroolefins 380

10.3.2 Multicomponent Reactions Initiated by the Knoevenagel Reaction 385

10.3.3 Multicomponent Reactions Based on the Mannich Reaction 388

10.3.4 Multicomponent Reactions Based on the Biginelli Reaction 392

10.3.5 Multicomponent Reactions Based on the Hantzsch Reaction 394

10.3.6 Multicomponent Reactions Based on the Strecker Reaction 395

10.3.7 Multicomponent Reactions Based on the Petasis Reaction 397

10.3.8 1,3-Dipolar Cycloaddition-Based Multicomponent Reactions 398

10.3.9 Miscellaneous Multicomponent Reactions 400

10.4 Conclusions 405

References 405

11 Metal-Catalyzed Enantio- and Diastereoselective C–C Bond-Forming Reactions in Domino Processes 419
Shinobu Takizawa and Hiroaki Sasai

11.1 Domino Reaction Initiated by C–C Bond Formation 419

11.1.1 Domino Reaction Initiated by Conjugate Addition 419

11.1.2 Domino Reaction Initiated by Cycloaddition 433

11.1.3 Domino Reaction Initiated by Carbometalation 435

11.2 Domino Reaction Initiated by C–H Bond Formation 435

11.2.1 Domino Reaction Initiated by Conjugate Addition 435

11.3 Domino Reaction Initiated by C–N Bond Formation 442

11.3.1 Domino Reaction Initiated by Imine Formation 442

11.3.2 Domino Reaction Based on Cycloaddition 443

11.4 Domino Reaction Initiated by C–O Bond Formation 445

11.4.1 Domino Reaction Initiated by Carbonyl Ylide Formation 445

11.4.2 Domino Reaction Initiated by Oxonium Ylide Formation 450

11.4.3 Domino Reaction Based on Cycloaddition 452

11.4.4 Domino Reaction Based on Pd(II)/Pd(IV) Catalysis 454

11.4.5 Domino Reaction Based on a Wacker Oxidation 454

11.5 Domino Reaction Initiated by C–B and C–Si Bond Formation 455

11.5.1 Domino Reaction Initiated by Conjugate Addition 456

11.6 Conclusion and Outlook 457

References 458

12 Domino Processes under Microwave Irradiation, High Pressure, and in Water 463
Bo Jiang, Shu-Jiang Tu, and Guigen Li

12.1 Introduction 463

12.2 Microwave-Assisted Domino Reactions 464

12.2.1 Intramolecular Domino Reactions under Microwave Heating 464

12.2.2 Two-Component Domino Reaction under Microwave Heating 465

12.2.3 Multicomponent Domino Reactions under Microwave Heating 472

12.3 Aqueous Domino Reactions 480

12.3.1 Two-Component Domino Reactions in Water 480

12.3.2 Multicomponent Domino Reaction in Water 484

12.4 High-Pressure-Promoted Domino Reactions 489

12.5 Conclusion and Outlook 491

Acknowledgments 492

References 492

13 Domino Reactions in Library Synthesis 497
Vincent Eschenbrenner-Lux, Herbert Waldmann, and Kamal Kumar

13.1 Introduction 497

13.2 Domino Reactions in Natural-Product-Inspired Compound Collection Syntheses 498

13.2.1 Coinage Metal-Catalyzed Domino Synthesis 498

13.2.2 Multicatalytic Domino Processes 500

13.2.3 Synthesis of Natural-Product-Inspired Centrocountins Using Domino Reactions 503

13.3 Domino Approaches Targeting Scaffold Diversity 506

13.3.1 Substrate-Based Approach: the Metathesis/Metathesis Domino Process 507

13.3.2 Reagent-Based Domino Approaches 509

13.3.3 Domino Reactions in the Build–Couple–Pair Approach for Library Synthesis 515

13.4 Solid-Phase Domino Syntheses of Compound Collections 516

13.5 Conclusion 519

References 520

14 Domino Reactions in the Total Synthesis of Natural Products 523
Svenia-C. D¨ufert, Judith Hierold, and Lutz F. Tietze

14.1 Cationic Domino Reactions 523

14.2 Anionic Domino Reactions 533

14.3 Radical Domino Reactions 549

14.4 Pericyclic Domino Reactions 551

14.5 Transition-Metal-Catalyzed Domino Reactions 554

14.6 Domino Reactions Initiated by Oxidation or Reduction 568

14.7 Conclusion 571

References 572

15 Multicomponent Domino Process: Rational Design and Serendipity 579
Qian Wang and Jieping Zhu

15.1 Introduction 579

15.2 Basic Considerations of MCRs 581

15.3 Substrate Design Approach in the Development of Novel MCRs 583

15.3.1 Chemistry of α-Isocyanoacetates 583

15.3.2 From α-Isocyanoacetates to α-Isocyanoacetamides 585

15.3.3 From α-Isocyanoacetamides to α-Isocyanoacetic Acids 589

15.3.4 Back to α-Isocyanoacetates 590

15.3.5 Chemistry of Oxazoles 593

15.3.5.1 Dienophile as an Additional Component 593

15.3.5.2 Using Dienophile-Containing Inputs 597

15.3.6 Serendipity 601

15.3.6.1 Groebke–Blackburn–Bienaym´e Reaction 601

15.3.6.2 One-Carbon Oxidative Homologation of Aldehydes to Amides 602

15.3.6.3 One-Carbon Oxidative Homologation of Aldehydes to α-Ketoamides 604

15.4 Conclusion 607

References 607

Index 611

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Lutz F. Tietze studied chemistry at the universities of Freiburg and Kiel, Germany, and obtained his doctorate under the supervision of Prof. B. Franck in 1968 in Kiel. He then worked as a research associate with Prof. G. Büchi at MIT, Cambridge, USA, as well as with Prof. A. Battersby in Cambridge, UK. Since 1978 he has been Professor and Head of the Institute of Organic and Biomolecular Chemistry at the Georg-August-University in Göttingen. His research focuses on the development of efficient and selective synthetic methods, combinatorial chemistry, the total synthesis of natural products and the design of new selective anticancer agents.

Professor Tietze has received many prizes, including the award for his book on "Reactions and Syntheses" by the Fonds der Chemischen Industrie, the Grignard-Wittig Prize of the Société Française de Chimie, the Prix Charles Mentzer of the Société de Chimie Thérapeutique France and the highly prestigious Emil Fischer Medal of the German Chemical Society. He was speaker of a Sonderforschungsbereich (Collaborative Research Centre), member of the DFG Fachkollegium and obtained several guest professorships. Moreover, he is chairman of the German Zentralverband der Chemie (Steering Committee of the German Chemical Societies), is member of a center of excellence and has been awarded in 2012 with the position of a Distinguished Research Professor. He has over 460 papers, 34 patents and four books to his name.

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