Catalytic Asymmetric Synthesis

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.

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