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 in keeping with Hydrogen Bonding: Elucidation of response Paths through 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 checklist: Chiral Bronsted Acids for C Organocatalysis.-

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M. Pihko et al. The effect of basic additive as well as water in proline catalyzed aldol reaction has been studied extensively [192]. Furthermore, Zhou and Shan disclosed that hydrogen bonding additives such as weak Brønsted acids successfully enhance both the efficiency and the selectivity of the reaction. They suggested that their hydrogen bonding BINOL additive enhanced the catalytic ability of proline by additional hydrogen bonding interactions between the catalyst, additive, and approaching substrate [68].

Some of these results are summarized in Table 1. 93 − 15 16 17 18 O N 19 O N 20 O N EtO 21 O N 22 Enamine Catalysis35 3535 The high reactivity of pyrrolidine-derived enamines can be explained by the increased propensity of five-membered rings to accept sp2-hybridized atoms into the ring compared to the six-membered rings. This phenomenon was first formulated and explained by Herbert C. Brown and coworkers in 1954 [45]. A sp2 hybridized nitrogen atom allows better overlap between the C = C p system and the nitrogen lone pair and therefore better delocalization of the nitrogen lone pair.

O Ph N H N H O Ph OH CO2Et CO2Et N H N H 48 OH O 49 Catalysts developed by Gong and co-workers N H O O N H Ph N H 50 Ph Ph OH O N H N H Ph Ph OH R2 R3 N H O R1 H A possible activation mode 51 Catalysts developed by Singh and co-workers Fig. 1 Ketone-Aldehyde and Ketone-Ketone Aldol Processes Typical starting materials, catalysts, and products of the enamine-catalyzed aldol reaction are summarized in Scheme 17. In proline-catalyzed aldol reactions, enantioselectivities are good to excellent with selected cyclic ketones, such as cyclohexanone and 4-thianone, but generally lower with acetone.

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