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

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

ISBN-10: 3642028144

ISBN-13: 9783642028144

Kerstin Etzenbach-Effers, Albrecht Berkessel: Non-Covalent Organocatalysis in keeping with Hydrogen Bonding: Elucidation of response Paths via 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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The structure of the amine component has a profound influence on the propensity to p-p delocalization. As an example, enamines derived from cyclic fivemembered ring amines, such as pyrrolidine, are more than thousand times more nucleophilic than those derived from six-membered ring amines. In a series of fundamental studies, the Mayr group has determined nucleophilicities of different enamines, ranging from highly reactive pyrrolidine-derived amines to relatively 34 P. M. Pihko et al. passive enaminones and pyrroles [44].

58] used a model system consisting of benzaldehyde and a modified Danishefsky’s diene, in which the trimethylsilyl group was replaced by a methyl group. They varied the aryl substituents of the TADDOL catalyst, and the results for the most enantioselective 1-naphthyl substituted catalyst were presented in detail.  18): the substrates and the core of TADDOL were treated with B3LYP/6-31G(d), while the substituents of the catalyst were modeled using semiempirical PM3 [61, 62] level. The energies of the optimized structures were determined by single point calculations with B3LYP/6-31G(d).

The first problem is a thermodynamic one. Most aldol reactions are reversible. Furthermore, the equilibrium is also just barely on the side of the products in the case of simple aldehyde-ketone aldol reactions [79, 80]. In the case of ketoneketone aldol reactions, the equilibrium generally lies on the side of starting materials (Scheme 14). Overall, this means that relatively high concentrations of starting materials should be used, and very often one of the components must be used in excess. A second, even more worrying problem is the side reaction, the formation of condensation products.

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


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