Domino Reactions (eBook)

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.

Preface
Introduction

TRANSITION METAL-CATALYZED CARBONYLATIVE DOMINO REACTIONS
Introduction
Transition Metal-Catalyzed Carbonylative Domino Reactions
Outlook

METATHESIS REACTIONS IN DOMINO PROCESSES
Domino Processes Featuring Solely Metathesis Events
Domino Processes Featuring Metathesis and Non-Metathesis Events
Conclusion and Outlook

C-H ACTIVATION REACTIONS IN DOMINO PROCESSES
Heck Reactions/C-H Activations
Carbopalladations and Aminopalladations of Alkynes/C-H Activations
Palladium-Catalyzed/Norbornene-Mediated ortho C-H Activations
Domino Reactions Involving Heteroatom-Directed C-H Activations
Conclusions

DOMINO REACTIONS INITIATED BY NUCLEOPHILIC SUBSTITUTION
Domino SN/Michael Addition and Related Reactions
Domino Reactions Initiated by Nucleophilic Ring Opening of Aziridines, Epoxides and Activated Cyclopropanes
Domino SN/Brook Rearrangements

RADICAL REACTIONS IN DOMINO PROCESSES
Introduction
Radical/Cation Domino Processes
Radical/Anionic Domino Processes
Domino Radical/Radical Process
Radical/Pericyclic Domino Processes
Asymmetric Radical Domino Processes
Conclusion and Outlook

PERICYCLIC REACTIONS IN DOMINO PROCESSES
Introduction
Cycloadditions
Sigmatropic Rearrangements
Electrocyclizations
Mixed Transformations
Concluding Remarks

MODERN DOMINO REACTIONS CONTAINING A MICHAEL ADDITION REACTION
Introduction
Formation of Acyclic Products
Formation of Carbocycles
Formation of O-Heterocycles
Formation of N-Heterocycles
Formation of S-Heterocycles
Formation of Heterocycles Containing Nitrogen and Oxygen

ALDOL REACTIONS IN DOMINO PROCESSES
Introduction
Domino Processes with the Aldol Reaction as First Step
Domino Processes with the Aldol Reaction as Subsequent Step
Conclusion and Outlook

OXIDATIONS AND REDUCTIONS IN DOMINO PROCESSES
Introduction
Domino Reactions Initiated by Oxidation or Reduction Reaction
Domino Reactions Having Oxidation in Middle of the Sequence
Domino Reactions Terminated by Oxidation or Reduction Reaction
Conclusion

ORGANOCATALYSIS IN DOMINO PROCESSES
Introduction
One and Two-Component Domino Reactions
Multicomponent Reactions
Conclusions

METAL-CATALYZED ENANTIO- AND DIASTEREOSELECTIVE C-C BOND FORMING REACTIONS IN DOMINO PROCESSES
Domino Reaction Initiated by C-C Bond Formation
Domino Reaction Initiated by C-H Bond Formation
Domino Reaction Initiated by C-N Bond Formation
Domino Reaction Initiated by C-O Bond Formation
Domino Reaction Initiated by C-B and C-Si Bond Formation
Conclusion and Outlook

DOMINO PROCESSES UNDER MICROWAVA IRRADIATION, HIGH PRESSURE, AND IN WATER
Introduction
Microwave-Assisted Domino Reactions
Aqueous Domino Reactions
High-Pressure-Promoted Domino Reactions
Conclusion and Outlook

DOMINO REACTIONS IN LIBRARY SYNTHESIS
Introduction
Domino Reactions in Natural-Product-Inspired Compound Collection Syntheses
Domino Approaches Targeting Scaffold Diversity
Solid-Phase Domino Syntheses of Compound Collections
Conclusion

DOMINO REACTIONS IN THE TOTAL SYNTHESIS OF NATURAL PRODUCTS
Cationic Domino Reactions
Anionic Domino Reactions
Radical Domino Reactions
Pericyclic Domino Reactions
Transition-Metal-Catalyzed Domino Reactions
Domino Reactions Initiated by Oxidation or Reduction
Conlcusion

MULTICOMPONENT DOMINO PROCESS: RATIONAL DESIGN AND SERENDIPITY
Introduction
Basic Considerations of MCRs
Substrate-Design Approach in the Development of Novel MCRs
Conclusion

Index