Catalytic Asymmetric Synthesis

Takahiko Akiyama, PhD, is Professor of Chemistry at Gakushuin University. Among his honors are the Nagoya Silver Medal (2012), the Arthur C. Cope Scholar Award (ACS) (2016), the Humboldt Research Award (2016), and the Chemical Society of Japan Award for Creative Work (2009).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 ixPreface to the First Edition xiList of Contributors xiiiPart I Asymmetric Organocatalysis 11 Asymmetric Enamine and Iminium Ion Catalysis 3Yujiro Hayashi2 Asymmetric Acid Organocatalysis 29Takahiko Akiyama3 Asymmetric Base Organocatalysis 81Azusa Kondoh and Masahiro Terada4 Asymmetric Phase-Transfer and Ion-Pair Organocatalyses 117Edward Miller, Patrick J. Moon, and F. Dean Toste5 Asymmetric Peptide Catalysis 157Kazuaki Kudo6 Asymmetric Carbene Catalysis: A Brief Highlight of Developments in the Past Decade 199Jia-Lei Yan, Hongling Wang, and Yonggui Robin Chi7 Asymmetric Hypervalent Iodine Catalysis 243Muhammet Uyanik and Kazuaki IshiharaPart II Asymmetric Photochemical Reactions and Photoredox Catalysis 2778 Asymmetric Visible-Light Photoredox Catalysis 279Jiyuan Lyu, Aurélie Claraz, and Géraldine Masson9 Asymmetric Photoredox Reactions without Photocatalysts 329Dengke Ma, Thomas Hin-Fung Wong, and Paolo Melchiorre10 Enantioselective Photochemical [2+2] Cycloaddition Reactions 355Freya M. Harvey and Thorsten BachPart III Asymmetric Synthesis Through C–H Bond Activation 38511 Asymmetric C–H Functionalization of C(sp2)–H Bond 387Uttam Dhawa, Tomasz Wdowik, and Lutz Ackermann12 Asymmetric C–H Functionalization of C(sp3)–H Bond 429Xiao Zhang, Yangyang Shen, Eva Bednáŕová, and Tomislav RovisPart IV Asymmetric Synthesis Through Carbon–Halogen Bond Formation and Enzyme Catalysis 49113 Asymmetric Carbon–Halogen Bond Forming Reactions (Excluding C–H Activation Processes) 493Santos Fustero, Attila M. Remete, Loránd Kiss, Mercedes Medio-Simón, Jorge Escorihuela, and Daniel M. Sedgwick14 Enzyme-Catalyzed Asymmetric Synthesis 531Gonzalo de Gonzalo and Andrés R. AlcántaraPart V Asymmetric Hydrogenation 55915 Asymmetric Hydrogenation 561Anton Vidal-Ferran, Arnald Grabulosa, Xavier Verdaguer, and Antoni RieraPart VI Asymmetric Carbon–Carbon Bond Forming Reactions Chapter 61716 Asymmetric Nucleophilic Addition to Ketones and Ketimines and ConjugateAddition Reactions 619Luo Ge and Syuzanna R. Harutyunyan17 Asymmetric Allylic Alkylation, Allylation, and Related Reactions 661Tyler J. Fulton, Yun E. Du, and Brian M. Stoltz18 Asymmetric Carbometallations Including Carbocyclizations 705Ken TanakaPart VII Asymmetric Synthesis of Non-Centro- Chiral Compounds 72719 Asymmetric Synthesis of Axially Chiral Compounds 729Shaohua Xiang, Jun Kee Cheng, and Bin Tan20 Asymmetric Synthesis of Planar Chiral and Helically Chiral Compounds 769Takanori ShibataPart VIII Asymmetric Polymerization 80321 Asymmetric Polymerization 805Jie Li and Xiao-Bing LuPart IX Asymmetric Catalysis in Continuous-Flow System 83122 Continuous-Flow Chemistry in Catalytic Asymmetric Synthesis 833Haruro Ishitani, Yuki Saito, and Shuˉ KobayashiIndex 869