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

  • ID: 2179938
  • Book
  • September 2009
  • 546 Pages
  • John Wiley and Sons Ltd
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This first comprehensive review of cinchona–based chiralilty transmitters and their applications covers all relevant topics, including ligands, organocatalysis and modern analytics. With contributions from academia and industry, each chapter summarizes the scope and limitations of the new methods and technologies, while the final chapter contains carefully selected representative Cinchona–promoted catalytic examples, organized by reaction types.

From the contents:

∗ An overview of chinchona alkaloids in chemistry

∗ Cinchona alkaloids and their derivatives as chirality inducers in metal–catalyzed asymmetric reactions

∗ Cinchona–based organocatalysts in enantioselective reactions

∗ Bifunctional cinchona–based organocatalysts

∗ Chiral phase–transfer catalysts derived from cinchona alkaloids

∗ Organic chemistry of cinchona alkaloids

∗ Resolution of racemates by Cinchona alkaloid and their derivatives

∗ Enantioselective analytics by Cinchona alkaloid and their derivatives

An indispensable handbook and "one–step" reference for those wishing to learn about the current state of this hot topic.

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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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"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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