Enantioselective Organocatalysis

Volume 1

Preface xvii

Part I Catalyst Structures 1

1 Privileged Catalyst Structures in Organocatalytic Reactions 3
Xiao Xiao, Xinyi Ren, Baoguo Zhao, and Kuiling Ding

2 Synthetic Peptide–Mediated Asymmetric Organocatalysis 45
Alexander J. Andre Cobb

3 Carbohydrates: A Promising Moiety for Organocatalysis 65
Nidhi Mishra, Sumit K. Singh, Mangal S. Yadav, and Vinod K. Tiwari

4 Chiral Polymer Catalysts 103
Shinichi Itsuno and Ikuhide Fujisawa

5 Emerging Organocatalyst Classes from Renewable Sources 125
Sara Meninno

6 Catalyst Recovery Strategies 165
Christine Tran and Petra Dunkel

7 In silico Catalyst Design Within Asymmetric Organocatalysis 225
Inigo Iribarren, Tim Renningtlotz, and Cristina Trujillo

8 A Critical Overview on Catalyst Synthesis 263
Alberto Lanfranco, Marco Rusconi, Jacopo Scarfiello, Annamaria Deagostino, and Polyssena Renzi

Part II Catalyst Functions 319

Aminocatalytic Transformations 321

9 Basicities and Nucleophilicities of N-Centered Organocatalysts 323
Herbert Mayr and Armin R. Ofial

10 Aminocatalysis 355
Fujie Tanaka

11 Cycloaddition Reactions with Primary and Secondary Amine Catalysts 415
Klara Aradi and Peter I. Dalko

12 Selected Examples of Aminocatalytic Direct Alpha-Heteroatom Functionalization, Alpha-Alkylation, and Allylation 455
Luca Deiana and Armando Cordova

13 Chiral Imidazolidinone (MacMillan’s) Catalyst 475
Rainer Mahrwald

14 Enantioselective Carbonyl Catalysis 511
Wen-Wen Chen and Baoguo Zhao

15 Nonclassical Hydrogen Bond (NCHB) Interactions in Enantioselective Organocatalysis 551
Manjaly J. Ajitha, Xingzhu Chen, and Kuo-Wei Huang

Volume 2

Preface xv

16 Progress in (Thio)urea- and Squaramide-Based Bronsted Acid and Bronsted Base Catalysts 571
Jesus M. Garcia and Antonia Mielgo

17 Strong Bronsted Acids 621
Takahiko Akiyama

18 Asymmetric Bronsted Base Catalysis 665
Azusa Kondoh and Masahiro Terada

Lewis Acid-Base Catalysis 719

19 Non-covalent Activations – Lewis Acids 721
Mariia Babkova and Rene Wilhelm

20 Lewis Base-Catalyzed Asymmetric Allylation, Propargylation, and Reduction of Carbonyl and Heterocarbonyl Compounds 763
Aleksandr E. Rubtsov and Andrei V. Malkov

21 Organocatalytic Transformations with Chiral Phosphines 803
Elizabeth A. Croll and Ohyun Kwon

22 Synthetic Transformations Assisted by Halogen, Chalcogen, and Pnictogen Bonding 849
Meghana P. Mohanan, Dragana Jovanovic, and Stefan M. Huber

23 N-Heterocyclic Carbenes in Asymmetric Organocatalysis: Methods and Applications 867
Alessandro Massi and Carmela De Risi

Catalysts Based on Electrostatic Interactions 909

24 Activation Modes in Anion-Binding Catalysis 911
Olaf Tjabben and Olga Garcia Mancheno

25 Transformations with Chiral Phase-Transfer Catalysts 945
Katharina Roser and Mario Waser

Part III Selected Organocatalytic Transformations 971

26 Asymmetric Organocatalytic Conjugate Additions 973
Alberto Vega-Penaloza, Albert Moyano, and Xavier Companyo

27 Organocatalytic Oxidations 1025
Efthymios T. Poursaitidis and Christoforos G. Kokotos

28 Organocatalytic Desymmetrizations 1063
Ramon Rios and Jan Veselý

29 Organocatalytic Dynamic Kinetic Resolution 1093
Helene Pellissier

Volume 3

Preface xvii

30 Increasing Complexity: Enantioselective Multicatalyzed Multistep Reactions 1169
Sandra Ardevines, Eugenia Marques-Lopez, and Raquel P. Herrera

31 Combined Power of Organocatalysis and Transition Metal Catalysis in Enantioselective Organic Synthesis 1201
Vladimir A. Larionov and Dmitrii S. Bolotin

32 Combining Organocatalysis and Biocatalysis in Multicatalytic Procedures 1231
Juan Manuel Coto-Cid and Gonzalo de Gonzalo

33 Light-Controlled Organocatalysis by Bifunctional Single-Catalyst Systems 1263
Alessa B. Rolka and Burkhard Konig

34 Dual Photo/Organocatalytic Strategies in Asymmetric Synthesis 1289
Sara Cuadros, Luca Dell’Amico, and Daniele Mazzarella

35 Recent Advances in Asymmetric Organocatalytic Inert C—H Bond Functionalization 1321
Yao Li and Sanzhong Luo

36 Miscellaneous Organocatalytic Redox and Electron Transfer Reactions 1347
Joshua L. Zhu and Karl A. Scheidt

37 Enantioselective Synthesis Enabled by Electrochemistry 1383
Ana Maria Faisca Phillips and Armando J. L. Pombeiro

Tuning Reactivity with the Reaction Media 1421

38 Asymmetric Organocatalysis in Water, Water in Asymmetric Organocatalysis 1423
Ciril Jimeno and Jordi Sola

39 Chiral Ionic Liquids and Deep Eutectic Solvents 1461
Sarah J. Burlingham, Jose A. Niguez, Francisco J. Sierra-Molero, Alejandro Torregrosa-Chinillach,

Part IV Applications 1487

40 Diastereodivergent and Enantiodivergent Synthesis with Organocatalysis 1489
Manisha Bihani, Pranjal P. Bora, and John C.-G. Zhao

41 Organocatalysis in Carbohydrate Synthesis 1535
Olivea M. Vasquez, Megan A. Sargent, and Clay S. Bennett

42 Stereocontrolled Organocatalysis in Polymer Synthesis 1567
Gabriela Garbonova, Louise Breloy, Haritz Sardon, and Fernando Vidal

43 Asymmetric Organocatalysis in Medicinal Chemistry 1603
Bo Han, Xiang Zhang, Xiang-Hong He, and Jun-Long li

44 Strategies Toward Asymmetric Organocatalysis at Parts-per-Million Loadings 1637
Choong Eui Song, Jin Hyun Park, and Sushovan Paladhi

45 Asymmetric Organocatalysis in Drug Discovery and the Patent Literature 1689
Anthony J. Burke and Elisabete P. Carreiro

Index 1719