Catalytic Asymmetric Synthesis (eBook)

IWAO OJIMA, PhD, a world-renowned leader in asymmetric catalysis, medicinal chemistry, and drug discovery, is the Distinguished Professor of Chemistry and the Director of the Institute of Chemical Biology and Drug Discovery at the State University of New York at Stony Brook. He is a recipient of numerous awards, including the Arthur C. Cope Scholar Award (ACS), the Chemical Society of Japan Award, and the E. B. Hershberg Award (ACS). He is a Fellow of the Guggenheim Foundation, the American Association for the Advancement of Science, and the New York Academy of Sciences. Dr. Ojima was inducted to the Medicinal Chemistry Hall of Fame (ACS) in 2006.

Preface ix

Preface to the Second Edition xi

Preface to the First Edition xiii

Contributors xv

1 Catalytic Asymmetric Synthesis in Nonconventional Media/Conditions 1
Chikako Ogawa and Shu Kobayashi

2 Asymmetric Organocatalysis 37

2A Enantioselective Organocatalysis Involving Iminium, Enamine, SOMO, and Photoredox Activation 39
Allan J. B. Watson and David W. C. MacMillan

2B Asymmetric Acid-Base Bifunctional Catalysis with Organic Molecules 59
Yi Wang and Li Deng

2C Asymmetric Phase-Transfer and Ion Pair Catalysis 95
Seiji Shirakawa and Keiji Maruoka

3 Chiral Lewis Acids and Brønsted Acids in Asymmetric Synthesis 119
Hisashi Yamamoto and Cheol Hong Cheon

4 Asymmetric Synthesis through C-H Activation 163
Huw M. L. Davies and Jørn Hansen

5 Asymmetric Carbon-Heteroatom Bond-Forming Reactions 227
Yoshiji Takemoto and Hideto Miyabe

6 Enzyme-Catalyzed Asymmetric Synthesis 269
Harald Gröger

7 Transition Metal-Catalyzed Homogeneous Asymmetric Hydrogenation 343
Gao Shang, Wei Li, and Xumu Zhang

8 Asymmetric Carbon-Carbon Bond-Forming Reactions 437

8A Catalytic Asymmetric Conjugate Addition 439
Jian-Xin Ji and Albert S. C. Chan

8B Enantioselective Allylic Substitutions with Carbon Nucleophiles 497
Günter Helmchen, Uli Kazmaier, and Sebastian Förster

8C Asymmetric Carbometallation and Carbocyclizations 643
Iwao Ojima, Joseph J. Kaloko, Stephen J. Chaterpaul, Yu-Han Gary Teng, and Chi-Feng Lin

8D Asymmetric Ene Reactions and Cycloadditions 683
Koichi Mikami and Kohsuke Aikawa

8E Catalytic Enantioselective Olefin Metathesis Reactions 739
Amir H. Hoveyda, Steven J. Malcolmson, Simon J. Meek, and Adil R. Zhugralin

9 Asymmetric Hydrosilylation of Carbon-Carbon Double Bonds and Related Reactions 771
Jin Wook Han and Tamio Hayashi

10 Asymmetric Carbonylations 799
Cyril Godard, Aurora Ruiz, Montserrat Diéguez, Oscar Pàmies, and Carmen Claver

11 Asymmetric Oxidations and Related Reactions 839
Kazuhiro Matsumoto and Tsutomu Katsuki

12 Asymmetric Amplification and Autocatalysis 891
Kenso Soai, Tsuneomi Kawasaki, and Takanori Shibata

13 Asymmetric Polymerization 931
Shingo Ito and Kyoko Nozaki

Index 987

"In summary, this is a comprehensive and up-to-date detailed textbook, excellent for reference, for gaining a rapid appreciation of what has been achieved in asymmetric catalysis, while suggesting the many directions it might be going in the future." (Applied Organometallic Chemistry, 6 March 2015)

"This is a well-prepared monograph that offers practical entries to the current literature for students or practitioners seeking a foundation in a particular area of asymmetric catalysis to support proposals or projects. . . Thus, the book has broad appeal; it should be useful for chemists at all levels, for graduate students and academic instructors to senior scientists and principal investigators." (Journal of Medicinal Chemistry, 16 June 2011)

"This third edition of Catalytic Asymmetric Synthesis remains at the forefront of literature resources, and should be added to all chemistry reference collections. Summing Up: Highly recommended. Upper-division undergraduates through professionals." (Choice, 1July 2011)

"An excellent working resource for academic researchers and industrial chemists alike . . . retaining the best of its predecessors but now thoroughly up to date, Catalytic Asymmetric Synthesis, Third Edition serves as an excellent desktop reference and text for researchers and students from the upper-level undergraduates through experienced professionals in industry or academia." (Organic Chemistry Portal, 1 May 2011)

"Overall, this book would be a useful addition to the library of a scientist engaged in catalysis in general and in asymmetric catalysis in particular. It is clearly a must-have for any comprehensive library.." (JACS, 2010)