Stereoselective Organocatalysis (eBook)

Bond Formation Methodologies and Activation Modes
eBook Download: PDF
2013 | 1. Auflage
674 Seiten
Wiley (Verlag)
978-1-118-60474-8 (ISBN)

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Stereoselective Organocatalysis -  Ramon Rios Torres
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Sets forth an important group of environmentally friendly organic reactions With contributions from leading international experts in organic synthesis, this book presents all the most important methodologies for stereoselective organocatalysis, fully examining both the activation mode as well as the type of bond formed. Clear explanations guide researchers through all the most important methods used to form key chemical bonds, including carbon-carbon (C C), carbon-nitrogen (C N), and carbon-halogen (C X) bonds. Moreover, readers will discover how the use of non-metallic catalysts facilitates a broad range of important reactions that are environmentally friendly and fully meet the standards of green chemistry. Stereoselective Organocatalysis begins with an historical overview and a review of activation modes in asymmetric organocatalysis. The next group of chapters is organized by bond type, making it easy to find bonds according to their applications. The first of these chapters takes a detailed look at the many routes to C C bond formation. Next, the book covers: Organocatalytic C N bond formation C O bond formation C X bond formation C S, C Se, and C B bond formation Enantioselective organocatalytic reductions Cascade reactions forming both C C bonds and C heteroatom bonds The final chapter is devoted to the use of organocatalysis for the synthesis of natural products. All the chapters in the book are extensively referenced, serving as a gateway to the growing body of original research reports and reviews in the field. Based on the most recent findings and practices in organic synthesis, Stereoselective Organocatalysis equips synthetic chemists with a group of organocatalytic reactions that will help them design green reactions and overcome many challenges in organic synthesis.

RAMON RIOS TORRES, PhD, is Reader in Organic Chemistry at the University of Southampton. With more than ninety peer-reviewed articles and several book chapters to his credit, Dr. Rios Torres devotes his research to the development of new asymmetric methods based on organocatalysis and organometallic chemistry as well as the application of these methods in total synthesis. Dr. Rios Torres is also the editor of The Pauson-Khand Reaction: Scope, Variations and Applications (Wiley).

PREFACE vii

CONTRIBUTORS ix

1. INTRODUCTION: A HISTORICAL POINT OF VIEW 1

Ramon Rios and Xavier Companyó

2. ACTIVATION MODES IN ASYMMETRIC ORGANOCATALYSIS
11

Albert Moyano

3. C-C BOND FORMATION BY ALDOL REACTION 81

Dorota Gryko and Dominika Walaszek

4. EXAMPLES OF METAL-FREE DIRECT CATALYTIC ASYMMETRIC
MANNICH-TYPE REACTIONS USING AMINOCATALYSIS 129

Armando Córdova

5. C-C BOND FORMATION BY MICHAEL REACTION 147

Yong Zhang and Wei Wang

6. C-C BOND FORMATION BY DIELS-ALDER AND OTHER
PERICYCLIC REACTIONS 205

Johan Franzén

7. N-HETEROCYCLIC CARBENE-CATALYZED C-C BOND FORMATION
231

Xiang-Yu Chen and Song Ye

8. a-ALKYLATION OF CARBONYL COMPOUNDS 267

Marek RemeS and Jan Vesely

9. OTHER REACTIONS FOR C-C BOND FORMATION 313

Yi-Xia Jia and Tiexin Zhang

10. CASCADE REACTIONS FORMING C-C BONDS 351

Ramon Rios, Jorge Esteban, and Xavier Companyó

11. ORGANOCATALYTIC C-N BOND FORMATION 381

Aitor Landa, Rosa López, Antonia Mielgo, Mikel Oiarbide,
and Claudio Palomo

12. C-O BOND FORMATION 433

José Alemán and Mariola Tortosa

13. CARBON-HALOGEN BOND FORMATION 465

Stacey E. Brenner-Moyer

14. C-OTHER ATOM BOND FORMATION (S, SE, B)
493

Giorgio Della Sala and Alessandra Lattanzi

15. ENANTIOSELECTIVE ORGANOCATALYTIC REDUCTIONS 529

Maurizio Benaglia, Martina Bonsignore, and Andrea Genoni

16. CASCADE REACTIONS FORMING BOTH C-C BOND AND
C-HETEROATOM BOND 559

Damien Bonne, Thierry Constantieux, Yoann Coquerel, and Jean
Rodriguez

17. ORGANOCATALYSIS IN THE SYNTHESIS OF NATURAL PRODUCTS
587

Yongcheng Ying and Xuefeng Jiang

INDEX 629

"The book is nicely structured and the chapters are
extensively supplemented by references, offering the reader a
practical overview of the field of asymmetric organocatalysis . . .
Congratulations to the editor and to all the authors for
this nice piece of work." (Angew. Chem. Int.
Ed, 1 October 2014)

Erscheint lt. Verlag 29.4.2013
Sprache englisch
Themenwelt Naturwissenschaften Chemie Organische Chemie
Naturwissenschaften Chemie Physikalische Chemie
Technik
Schlagworte catalysis • Chemie • Chemistry • Katalyse • Nachhaltige u. Grüne Chemie • Nachhaltige u. Grüne Chemie • Organic Chemistry • Organische Chemie • Sustainable Chemistry & Green Chemistry
ISBN-10 1-118-60474-1 / 1118604741
ISBN-13 978-1-118-60474-8 / 9781118604748
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