9783527308064

In the very first book on this hot topic, the expert editors and authors present a comprehensive overview of these elegant reactions. From the contents: * Organoboron compounds * Free-radical mediated multicomponent coupling reactions * Applications in drug discovery * Metal catalyzed reactions * Total synthesis of natural products * Asymmetric isocyanide-based reactions * The Biginelli reaction * Asymmetric isocyanide-based reactions * The Domino-Knoevenagel-Hetero-Diels-Alder Reaction and related transformations * Catalytic asymmetric reactions * Algorithm based methods for discovering novel reactions * Post-condensation modifications of the Passerini and Ugi reactions An essential reference for organic and catalytic chemists, and those working in organometallics both in academia and industry.

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Jieping Zhu received his BSc from Hanzhou Normal University in 1984 and his MSc from Lanzhou University in 1987 under Professor Y. -L. Li. In 1991, he obtained his PhD from the Université Paris XI under Professor H. -P. Husson. After 18 months post-doctoral research with Professor Sir D. H. R. Barton at Texas A & M University in USA, he joined the Institut de Chimie des Substances Naturelles (CNRS) in December 1992, where he is currently Director of Research. His main research interests center on the development of novel synthetic methods, their application in the synthesis of bioactive natural products, and the design of novel multicomponent reactions. Dr. Zhu has published over 110 research papers. Hugues Bienaymé gained his PhD in organic chemistry at the university of Paris under Professor A. Lubineau, than took up a post-doctoral position at the University of Geneva under the supervision of Professor W. Oppolzer. He joined Rhône Poulenc (Aventis) in 1991 where he held various research positions in process and discovery chemistry. From 1995 to 2000 he was head of the combinatorial and discovery chemistry group for the company's central research department, developing multi-component condensations as a general tool to accelerate drug discovery. In 1996 the company awarded him the title "associate professor". In 2001, Dr. Bienaymé founded Chrysalon, a start-up in the field of combinatorial chemistry. After the company's merger in 2003, he became managing director and CSO of Urogene, a biotech company dedicated to discovering new drugs in urology. Hugues Bienaymé is the author or co-author of more than 40 publications and patents.

Preface.

Contributors.

1 Asymmetric Isocyanide-based MCRs (Luca Banfi, Andrea Basso, Giuseppe Guanti, and Renata Riva).

1.1 Introduction.

1.2 Racemization Issues.

1.3 Asymmetric Passerini Reactions.

1.4 Asymmetric Intermolecular Ugi Reactions.

1.5 Asymmetric Intramolecular Ugi Reactions.

1.6 Other Asymmetric Isonitrile-based Multicomponent Reactions.

2 Post-condensation Modifications of the Passerini and Ugi Reactions (Stefano Marcaccini and Toma´s Torroba).

2.1 Convertible Isocyanides.

2.2 I-MCR Post-condensation Reactions in Synthesis of Open-chain Products.

2.3 I-MCR Post-condensation Reactions in the Synthesis of Heterocycles.

3 The Discovery of New Isocyanide-based Multicomponent Reactions (Alexander Dömling).

3.1 Introduction.

3.2 New MCRs.

3.3 Random Discovery.

3.4 Combinatorial MCR Discovery.

3.5 Discovery by Design.

3.6 The Union of MCRs.

3.7 Outlook.

4 The Biginelli Reaction (C. Oliver Kappe).

4.1 Introduction.

4.2 Mechanistic Studies.

4.3 Reaction Conditions.

4.4 Building Blocks.

4.5 Synthesis of Combinatorial Libraries.

4.6 Alternative Synthetic Strategies.

4.7 Related Multicomponent Reactions.

4.8 Asymmetric Biginelli Reactions.

4.9 Conclusion.

5 The Domino-Knoevenagel-hetero-Diels–Alder Reaction and Related Transformations (Lutz F. Tietze and Nils Rackelmann).

5.1 Introduction 121

5.2 Two-component Reactions with an Intramolecular Cycloaddition 123

5.3 Three- and Four-component-domino-Knoevenagel-hetero-Diels–Alder Reaction.

5.4 Synthesis of Azasteroids and Steroid Alkaloids.

5.5 Domino-Knoevenagel-carbon-Diels–Alder Reactions.

6 Free-radical-mediated Multicomponent Coupling Reactions (Mami Tojino and Ilhyong Ryu).

6.1 Introduction.

6.2 Hetero-multicomponent Coupling Reactions.

6.3 Multicomponent Coupling Reactions Mediated by Group 14 Radicals.

6.4 Multicomponent Coupling Reactions Involving Electron-transfer Processes.

6.5 Conclusions.

7 Multicomponent Reactions with Organoboron Compounds (Nicos A. Petasis).

7.1 Introduction.

7.2 MCRs Involving Amines and Aldehydes or Ketones.

7.3 MCRs Involving Organoboron Compounds.

7.4 Summary and Conclusion.

8 Metal-catalyzed Multicomponent Reactions (Geneviève Balme, Didier Bouyssi, and Nuno Monteiro).

8.1 Introduction.

8.2 Vicinal Difunctionalization of Alkenes and Acetylenes via Intermolecular Carbometallation.

8.3 Reactions Involving p-Allyl Palladium Species as Intermediates.

8.4 Cross-coupling Reactions of Terminal Alkynes with Organic Halides.

8.5 Cyclofunctionalization of Alkynes and Alkenes Bearing Pendant Nucleophiles.

8.6 Transition-metal-catalyzed Reactions Based on the Reactivity of Isonitriles.

8.7 Pd/Cu-catalyzed Synthesis of Triazoles.

8.8 Reactions Involving Imines as Intermediates.

8.9 Cycloadditions and Related Reactions.

8.10 Three-component Reactions Involving Metallocarbenes.

8.11 Metathesis.

8.12 Concluding Remarks.

9 Catalytic Asymmetric Multicomponent Reactions (Jayasree Seayad and Benjamin List).

9.1 Introduction.

9.2 Mannich Reactions.

9.3 Three-component Aldolizations.

9.4 Three-component Tandem Michael–Aldol Reaction.

9.5 Passerini Reaction.

9.6 Strecker Reaction.

9.7 Aza Morita–Baylis–Hillman Reactions.

9.8 Domino-Knoevenagel-hetero-Diels–Alder-type Reactions.

9.9 Three-component Hetero-[4+2]-cycloaddition–Allylboration Tandem Reaction.

9.10 Addition of Alkylzincs.

9.11 Alkyne Nucleophiles.

9.12 Coupling of Alkynes, Imines and Organoboranes.

9.13 Free-radical Reactions.

9.14 Summary and Outlook.

10 Algorithm-based Methods for the Discovery of Novel Multicomponent Reactions (Lutz Weber).

10.1 Introduction.

10.2 A Definition – What Are Novel MCRs.

10.3 Unexpected Products Yield Novel MCRs.

10.4 Experimental Designs to Search for New MCRs.

10.5 Computational Methods of Finding Novel MCRs.

10.6 Combinatorial Optimization of Reaction Conditions.

11 Applications of Multicomponent Reactions in Drug Discovery – Lead Generation to Process Development (Christopher Hulme).

11.1 Introduction.

11.2 Hantsch (1882) and Biginelli (1893) Reactions.

11.3 Passerini Reaction (1921).

11.4 Ugi Reaction (1958).

11.5 Constrained Ugi Adducts from Bi-functional Precursors.

11.6 Gewald Reaction (1965).

11.7 Applications of MCRs to Process Development.

11.8 Conclusions.

12 Multicomponent Reactions in the Total Synthesis of Natural Products (Barry B. Touré and Dennis G. Hall).

12.1 Introduction.

12.2 Cyclopentane-containing Natural Products.

12.3 Terpenoids.

12.4 Polyenes and Polyynes.

12.5 Oxacyclic Natural Products.

12.6 Polyols and Polysaccharides.

12.7 Lignans.

12.8 Alkaloids.

12.9 Peptides.

12.10 Other Natural Products.

12.11 Conclusion.

13 The Modified Sakurai and Related Reactions (Thomas Jacques, István E. Markó, and Jiří Pospíšil).

13.1 Introduction.

13.2 The Sakurai–Hosomi Reaction.

13.3 The Silyl-modified Sakurai Reaction.

13.4 Intramolecular Sakurai Condensation.

Index.

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Multicomponent Reactions

Multicomponent Reactions

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