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Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis

Choong Eui Song (Editor)
ISBN: 978-3-527-32416-3
546 pages
December 2009
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis (352732416X) cover image


This comprehensive review of cinchona-based chiralilty inducers and their applications covers every topic, including ligands, immobilization and organocatalysis. Each chapter summarizes the scope and limitations of the new methods and technologies, while the final chapter contains carefully selected working procedures of cinchona alkaloid-promoted reactions organized according to reaction type.
Invaluable reading for anyone wanting to learn about the current state of this hot topic.
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Table of Contents



List of Contributors.

1 An Overview of Cinchona Alkaloids in Chemistry (Choong Eui Song).

Part One: Cinchona Alkaloid Derivatives as Chirality Inducers in Metal-Catalyzed Reactions.

2 Cinchona Alkaloids as Chirality Transmitters in Metal-Catalyzed Asymmetric Reductions (Hans-Ulrich Blaser).

3 Cinchona Alkaloids as Chiral Ligands in Asymmetric Oxidations (David J. Ager).

4 Cinchona Alkaloids and their Derivatives as Chirality Inducers in Metal-Promoted Enantioselective Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions (Ravindra R. Deshmukh, Do Hyun Ryu, and Choong Eui Song).

Part Two: Cinchona Alkaloid Derivatives as Chiral Organocatalysts.

5 Cinchona-Based Organocaalysts for Asymmetric Oxidations and Reductions (Ueon Sang Shin, Je Eun Lee, Jung Woon Yang, and Choong Eui Song).

6 Cinchona-Catalyzed Nucleophilic α-Substitution of Carbonyl Derivatives (Hyeung-geun Park and Byeong-Seon Jeong).

7Cinchona-Mediated Enantioselective Protonations (Jacques Rouden).

8 Cinchona-Catalyzed Nucleophilic 1,2-Addition to C=O and C=N Bonds (Hyeong Bin Jang, Ji Woong Lee, and Choong Eui Song).

9 Cinchona-Catalyzed Nucleophilic Conjugate Addition to Electron-Deficient C=C Double Bonds (Ji Woong Lee, Hyeong Bin Jang, and Choong Eui Song).

10 Cinchona-Catalyzed Cycloaddition Reactions (Yan-Kai Liu and Ying-Chun Chen).

11 Cinchona-Based Organocatalysts for Desymmetrization of meso-Compounds and (Dynamic) Kinetic Resolution of Racemic Compounds (Ji Woong Lee, Hyeong Bin Jang, Je Eun Lee, and Choong Eui Song).

Part Three: Organic Chemistry of Cinchona Alkaloids.

12 Organic Chemistry of Cinchona Alkaloids (Hans Martin Rudolf Hoffmann and Jens Frackenpohl).

Part Four: Cinchona Alkaloid and Their Derivatives in Analytics.

13 Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives (Karol Kacprzak and Jacek Gawronski).

Appendix: Tabular Survey of Selected Cinchona-Promoted Asymmetric Reactions(Ji Woong Lee and Choong Eui Song).


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Author Information

Choong Eui Song has been a full Professor at Sungkyunkwan University since 2004. He received his B.S. in 1980 from Chungang University and obtained a Diploma (1985) and a Ph.D. (1988) at RWTH Aachen in Germany. After completing his Ph.D. he worked as a Principal Research Scientist at the Korea Institute of Science and Technology (KIST). In 2001 he was appointed as head of the national research laboratory for Green Chirotechnology in Korea. In 2004 he moved to his current position and in 2006 he was appointed as a director at the Research Institute of Advanced Nanomaterials and Institute of Basic Sciences in Sungkyunkwan University. His research interests focus on asymmetric catalysis, ionic liquid chemistry and nanochemistry. He received the Scientist of the Month Award from the Ministry of Science and Technology in Korea (2001).
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"There has been a real hunger for this book amongst research fraternity and innovators. The book is sure to become dogeared as it is read, used, and reread to help evaluators conduct their work in a manner consistent with the complexity of the challenges they are addressing." (Current Engineering Practice, 2010)

"Process chemists will find much of interest in this multi-author work." (Organic Process Research & Development Journal, 2010)

"Novices as well as experts in the area of asymmetric catalysis will find this book to be a very valuable resource." (JACS, 2010)

"Cinchona Alkaloids in Synthesis & Catalysis will be warmly welcomed by many researchers, as the use of cinchona alkaloids continues to have a major impact on chemistry research. It represents the first attempt to comprehensively describe the many facets of the chemistry of this privileged compound class, which has been generously provided by nature. Song has succeeded in providing the synthesis community with a high-quality source of teaching materials as well as a useful handbook for scientists working in the exciting and fast developing field of cinchona-based asymmetric catalysis. This book will be a valuable addition to many libraries, whether personal, academic, or industrial." (Angewandte Chemie, 2010)
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