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Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes

ISBN: 978-1-118-20353-8
674 pages
June 2013
Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes (1118203534) cover image

Description

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.

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Table of Contents

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 Remeš and Jan Veselý

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

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Author Information

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).

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Reviews

“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)

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