35537-88-3Relevant academic research and scientific papers
Bifunctional organocatalysts based on a carbazole scaffold for the synthesis of the Hajos-Wiechert and Wieland-Miescher ketones
Rubio, Omayra H.,Fuentes De Arriba, ángel L.,Monleón, Laura M.,Sanz, Francisca,Simón, Luis,Alcázar, Victoria,Morán, Joaquín R.
supporting information, p. 1297 - 1303 (2015/03/05)
Several bifunctional organocatalysts based on a carbazole scaffold containing a chiral amine and a synthetic oxyanion-hole have been synthesized and successfully applied to the synthesis of the Hajos-Wiechert and Wieland-Miescher ketones (up to 99% ee). Both enamine activation and H-bonding donor ability of these catalysts were evaluated by preparing catalysts differing in the nature of the amine [(R,R)-cyclohexanediamine or l-proline], the H-bond donor functional group (sulfonamide or amide) and the number of NH bonds. Modeling studies and an X-ray structure fully support the obtained results.
Proline imidazolidinones and enamines in Hajos-Wiechert and Wieland-Miescher ketone synthesis
de Arriba, ángel L. Fuentes,Simón, Luis,Raposo, César,Alcázar, Victoria,Morán, Joaquín R.
scheme or table, p. 4841 - 4845 (2009/10/02)
Readily available aromatic prolinamides obtained from the acid chloride of proline hydrochloride and anilines induce large enantiomeric excesses in intramolecular aldol condensations. Imidazolidinones derived from the reaction of the catalyst and enamines
