100125-26-6Relevant articles and documents
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.
, p. 1297 - 1303 (2015)
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.
