|
|||||
|
|
Gelatin Protein‐Mediated Direct Aldol Reaction |
|
| Authors: | Dennis Kühbeck Vicente Gotor‐Fernández David Díaz Díaz |
| Institution: | 1. Universit?t Regensburg, Institut für Organische Chemie, Universit?tsstrasse 31, DE‐93053 Regensburg, (phone: +49‐941‐943‐4373;2. fax: +49‐941‐943‐4121);3. Universidad de Oviedo, Departamento de Química Orgánica e Inorgánica, Avenida Julián Clavería s/n, ES‐33071 Oviedo;4. IQAC‐CSIC, Jordi Girona 18‐26, ES‐08034 Barcelona |
| Abstract: | Gelatin protein was found to catalyze the aldol reaction between cyclohexanone and different aromatic aldehydes under mild reaction conditions. The aldol additions carried out in DMSO at 37° yielded the addition products with moderate diastereoselectivities favoring the syn isomers. Appropriate control experiments demonstrated the activity of the protein in the aldol reaction. The kinetic study of the model reaction between 4‐nitrobenzaldehyde and cyclohexanone established a first‐order rate constant k=(7.4±0.5)×10?3 h?1. Moreover, the scale‐up of the process was successfully achieved at 1‐g scale in a yield comparable to that in small scale. |
| Keywords: | Aldol reaction Gelatin C C Bond formation Biocatalysis |