Asymmetric Organocatalysis by Daniela Kampen, Corinna M. Reisinger, Benjamin List (auth.),

By Daniela Kampen, Corinna M. Reisinger, Benjamin List (auth.), Benjamin List (eds.)

Kerstin Etzenbach-Effers, Albrecht Berkessel: Non-Covalent Organocatalysis according to Hydrogen Bonding: Elucidation of response Paths by means of Computational Methods.- Petri M. Pihko, Inkeri Majander, and Anniina Erkkilä: Enamine Catalysis.- Jennifer L. Moore, Tomislav Rovis: Lewis Base Catalysts 6: Carbene Catalysts.- Amal Ting, Jennifer M. Goss, Nolan T. McDougal, and Scott E. Schaus: Brønsted Base Catalysts.- O. Andrea Wong, Yian Shi: Chiral Ketone and Iminium Catalysts for Olefin Epoxidation.- Alan C. Spivey, Stellios Arseniyadis: Amine, Alcohol and Phosphine Catalysts for Acyl move Reactions.- John B. Brazier, Nicholas C.O. Tomkinson: Lewis Base Catalysts 2 Secondary and first Amine Catalysts for Iminium Catalysis.- Oksana Sereda, Sobia Tabassum, and René Wilhelm: Lewis Acid Organocatalysts.- Daniela Kampen , Corinna M. Reisinger , and Benjamin record: Chiral Bronsted Acids for C Organocatalysis.-

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In general, yields and enantioselectivities of proline-catalyzed Mannich reactions are very high. Initially, the reactions were restricted to imines bearing an aromatic N-substituent, such as the p-methoxyphenyl (PMP) group. This restriction considerably limited the usefulness of the protocol, because relatively 52 P. M. Pihko et al. harsh conditions were required for the removal of the N-aryl protecting group. However, recent developments by List and Enders [245] have expanded the scope of the imine acceptors, and N-Boc-protected imines can now be used routinely [246].

Only a few reactions with a purely external cocatalytic acid source have been published, and very few screening studies of the cocatalysts are available. Barbas and coworkers studied the effects of Lewis and Brønsted acids in the pyrrolidine-catalyzed aldol reaction [69]. They observed that acetic acid provided over twofold greater initial reaction rates compared to the same reaction without acid. Interestingly, stronger acids such as TfOH, PTSA and CSA gave slower reaction rates. Subsequently, Peng and coworkers disclosed beneficial effect of substituted phenols in the same reaction [70].

13 Aggregation-induced hydrogen bonding enhancement of HFIP Noncovalent Organocatalysis Based on Hydrogen Bonding 19 for the calculations in which one to four molecules of HFIP are added to the transition state of the reaction. The first quantum-chemical investigation of the mechanism of olefin epoxidation in fluoroalcohols was carried out by Shaik et al. [54]. In the absence of kinetic data, a monomolecular mode of activation by the fluorinated alcohols for all reaction pathways was assumed [54].

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