Catalytic Asymmetric Synthesis

Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today

This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include:

• Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis
• C–H bond functionalization reactions
• Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions
• Axially chiral compounds

Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.

Takahiko Akiyama, PhD is Professor of Chemistry at Gakushuin University. Among his honors are Nagoya silver medal, the Arthur C. Cope Scholar Award (ACS), and the Humboldt Research Award.

Iwao Ojima, PhD is University Distinguished Professor and Director of the Institute of Chemical Biology and Drug Discovery at the State University of New York, Stony Brook. He is a recipient of numerous awards, including the Arthur C. Cope Scholar Award (1994), E. B. Hershberg Award (2001), ACS Award for Creative Work in Fluorine Chemistry (2013), Ernest Guenther Award (2019) (all from ACS) and the Chemical Society of Japan Award (1999).

Preface ix

Preface to the First Edition xi

List of Contributors xiii

Part I Asymmetric Organocatalysis 1

1 Asymmetric Enamine and Iminium Ion Catalysis 3
Yujiro Hayashi

2 Asymmetric Acid Organocatalysis 29
Takahiko Akiyama

3 Asymmetric Base Organocatalysis 81
Azusa Kondoh and Masahiro Terada

4 Asymmetric Phase-Transfer and Ion-Pair Organocatalyses 117
Edward Miller, Patrick J. Moon, and F. Dean Toste

5 Asymmetric Peptide Catalysis 157
Kazuaki Kudo

6 Asymmetric Carbene Catalysis: A Brief Highlight of Developments in the Past Decade 199
Jia-Lei Yan, Hongling Wang, and Yonggui Robin Chi

7 Asymmetric Hypervalent Iodine Catalysis 243
Muhammet Uyanik and Kazuaki Ishihara

Part II Asymmetric Photochemical Reactions and Photoredox Catalysis 277

8 Asymmetric Visible-Light Photoredox Catalysis 279
Jiyuan Lyu, Aurélie Claraz, and Géraldine Masson

9 Asymmetric Photoredox Reactions without Photocatalysts 329
Dengke Ma, Thomas Hin-Fung Wong, and Paolo Melchiorre

10 Enantioselective Photochemical [2+2] Cycloaddition Reactions 355
Freya M. Harvey and Thorsten Bach

Part III Asymmetric Synthesis Through C–H Bond Activation 385

11 Asymmetric C–H Functionalization of C(sp2)–H Bond 387
Uttam Dhawa, Tomasz Wdowik, and Lutz Ackermann

12 Asymmetric C–H Functionalization of C(sp3)–H Bond 429
Xiao Zhang, Yangyang Shen, Eva Bednáŕová, and Tomislav Rovis

Part IV Asymmetric Synthesis Through Carbon–Halogen Bond Formation and Enzyme Catalysis 491

13 Asymmetric Carbon–Halogen Bond Forming Reactions (Excluding C–H Activation Processes) 493
Santos Fustero, Attila M. Remete, Loránd Kiss, Mercedes Medio-Simón, Jorge Escorihuela, and Daniel M. Sedgwick

14 Enzyme-Catalyzed Asymmetric Synthesis 531
Gonzalo de Gonzalo and Andrés R. Alcántara

Part V Asymmetric Hydrogenation 559

15 Asymmetric Hydrogenation 561
Anton Vidal-Ferran, Arnald Grabulosa, Xavier Verdaguer, and Antoni Riera

Part VI Asymmetric Carbon–Carbon Bond Forming Reactions Chapter 617
16 Asymmetric Nucleophilic Addition to Ketones and Ketimines and Conjugate

Addition Reactions 619
Luo Ge and Syuzanna R. Harutyunyan

17 Asymmetric Allylic Alkylation, Allylation, and Related Reactions 661
Tyler J. Fulton, Yun E. Du, and Brian M. Stoltz

18 Asymmetric Carbometallations Including Carbocyclizations 705
Ken Tanaka

Part VII Asymmetric Synthesis of Non-Centro- Chiral Compounds 727

19 Asymmetric Synthesis of Axially Chiral Compounds 729
Shaohua Xiang, Jun Kee Cheng, and Bin Tan

20 Asymmetric Synthesis of Planar Chiral and Helically Chiral Compounds 769
Takanori Shibata

Part VIII Asymmetric Polymerization 803

21 Asymmetric Polymerization 805
Jie Li and Xiao-Bing Lu

Part IX Asymmetric Catalysis in Continuous-Flow System 831

22 Continuous-Flow Chemistry in Catalytic Asymmetric Synthesis 833
Haruro Ishitani, Yuki Saito, and Shuˉ Kobayashi

Index 869

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