Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes

Sets forth an important group of environmentally friendly organic reactions With contributions from leading international experts in organic synthesis, this book presents all the most important methodologies for stereoselective organocatalysis, fully examining both the activation mode as well as the type of bond formed. Clear explanations guide researchers through all the most important methods used to form key chemical bonds, including carbon-carbon (C–C), carbon-nitrogen (C–N), and carbon-halogen (C–X) bonds. Moreover, readers will discover how the use of non-metallic catalysts facilitates a broad range of important reactions that are environmentally friendly and fully meet the standards of green chemistry. Stereoselective Organocatalysis begins with an historical overview and a review of activation modes in asymmetric organocatalysis. The next group of chapters is organized by bond type, making it easy to find bonds according to their applications. The first of these chapters takes a detailed look at the many routes to C–C bond formation. Next, the book covers: Organocatalytic C–N bond formation C–O bond formation C–X bond formation C–S, C–Se, and C–B bond formation Enantioselective organocatalytic reductions Cascade reactions forming both C–C bonds and C–heteroatom bonds The final chapter is devoted to the use of organocatalysis for the synthesis of natural products. All the chapters in the book are extensively referenced, serving as a gateway to the growing body of original research reports and reviews in the field. Based on the most recent findings and practices in organic synthesis, Stereoselective Organocatalysis equips synthetic chemists with a group of organocatalytic reactions that will help them design green reactions and overcome many challenges in organic synthesis.

Preface List of Contributors Foreword 1 Introduction: A historical point of view Ramon Rios and Xavier Companyo 2 Activation Modes in Asymmetric Organocatalysis Albert Moyano 3 C–C bond formation   3.1 By aldol reaction Dorota Gryko and Dominika Walaszek 3.2 Examples of Metal–Free Direct Catalytic Asymmetric Mannich–Type Reactions using Aminocatalysis Armando Cordova 3.3 By Michael reaction Yong Zhang and Wei Wang 3.4 By Diels Alder and Other Pericyclic Reactions Johan Franzén 3.5 N–Heterocyclic carbene–catalyzed C–C bond formation Xiang–Yu Chen, Song Ye 3.6 α–Alkylation of carbonyl compounds Marek Remeš and Jan Veselý 3.7 Other Reactions Yi–Xia JIA and Tiexin Zhang 3.8 Cascade Reactions forming C–C bonds Ramon Rios, Jorge Esteban and Xavier Companyó 4. Organocatalytic C–N bond formation Aitor Landa, Rosa López, Antonia Mielgo, MikelOiarbide and Claudio Palomo 5. C–O bond formation José Alemán, Mariola Tortosa 6. Carbon–halogen bond formation Stacey E. Brenner–Moyer 7. C–other atom bond formation (S, Se, B) Giorgio Della Sala, and Alessandra Lattanzi 8. Enantioselectiveorganocatalytic reductions Maurizio Benaglia, Martina Bonsignore and Andrea Genoni 9. Cascade reactions forming both C–C bond and C–heteroatom bond Damien Bonne, Thierry Constantieux, Yoann Coquerel and Jean Rodriguez 10. Organocatalysis in the Synthesis of Natural Products Yongcheng Ying and Xuefeng Jiang

RAMON RIOS TORRES, PhD, is Reader in Organic Chemistry at the University of Southampton. With more than ninety peer-reviewed articles and several book chapters to his credit, Dr. Rios Torres devotes his research to the development of new asymmetric methods based on organocatalysis and organometallic chemistry as well as the application of these methods in total synthesis. Dr. Rios Torres is also the editor of The Pauson-Khand Reaction: Scope, Variations and Applications (Wiley).