Stereoselective Organocatalysis

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 vii CONTRIBUTORS ix 1. INTRODUCTION: A HISTORICAL POINT OF VIEW 1 Ramon Rios and Xavier Companyó 2. ACTIVATION MODES IN ASYMMETRIC ORGANOCATALYSIS 11 Albert Moyano 3. C–C BOND FORMATION BY ALDOL REACTION 81 Dorota Gryko and Dominika Walaszek 4. EXAMPLES OF METAL-FREE DIRECT CATALYTIC ASYMMETRIC MANNICH-TYPE REACTIONS USING AMINOCATALYSIS 129 Armando Córdova 5. C–C BOND FORMATION BY MICHAEL REACTION 147 Yong Zhang and Wei Wang 6. C–C BOND FORMATION BY DIELS–ALDER AND OTHER PERICYCLIC REACTIONS 205 Johan Franzén 7. N-HETEROCYCLIC CARBENE-CATALYZED C–C BOND FORMATION 231 Xiang-Yu Chen and Song Ye 8. a-ALKYLATION OF CARBONYL COMPOUNDS 267 Marek Remeš and Jan Veselý 9. OTHER REACTIONS FOR C–C BOND FORMATION 313 Yi-Xia Jia and Tiexin Zhang 10. CASCADE REACTIONS FORMING C–C BONDS 351 Ramon Rios, Jorge Esteban, and Xavier Companyó 11. ORGANOCATALYTIC C–N BOND FORMATION 381 Aitor Landa, Rosa López, Antonia Mielgo, Mikel Oiarbide, and Claudio Palomo 12. C–O BOND FORMATION 433 José Alemán and Mariola Tortosa 13. CARBON–HALOGEN BOND FORMATION 465 Stacey E. Brenner-Moyer 14. C–OTHER ATOM BOND FORMATION (S, SE, B) 493 Giorgio Della Sala and Alessandra Lattanzi 15. ENANTIOSELECTIVE ORGANOCATALYTIC REDUCTIONS 529 Maurizio Benaglia, Martina Bonsignore, and Andrea Genoni 16. CASCADE REACTIONS FORMING BOTH C–C BOND AND C–HETEROATOM BOND 559 Damien Bonne, Thierry Constantieux, Yoann Coquerel, and Jean Rodriguez 17. ORGANOCATALYSIS IN THE SYNTHESIS OF NATURAL PRODUCTS 587 Yongcheng Ying and Xuefeng Jiang INDEX 629