Domino reactions : concepts for efficient organic synthesis

edited by Lutz F. Tietze

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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[目次]

  • 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 alpha,beta-Unsaturated Aldehydes 371 10.3.1.2 Michael Reactions of Other alpha,beta-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 alpha-Isocyanoacetates 583 15.3.2 From alpha-Isocyanoacetates to alpha-Isocyanoacetamides 585 15.3.3 From alpha-Isocyanoacetamides to alpha-Isocyanoacetic Acids 589 15.3.4 Back to alpha-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 alpha-Ketoamides 604 15.4 Conclusion 607 References 607 Index 611

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この本の情報

書名 Domino reactions : concepts for efficient organic synthesis
著作者等 Tietze, Lutz-Friedjan
Tietze Lutz F.
出版元 Wiley-VCH
刊行年月 c2014
ページ数 xxiii, 621 p.
大きさ 25 cm
ISBN 9783527334322
NCID BB14812231
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言語 英語
出版国 ドイツ
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