33879-04-8Relevant articles and documents
Catalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by cis- and trans-4,5-methanoprolines: Sensitivity of proline catalysis to pyrrolidine ring conformation
Cheong, Paul Ha-Yeon,Houk,Warrier, Jayakumar S.,Hanessian, Stephen
, p. 1111 - 1115 (2004)
Methanoprolines are found to be catalysts for the Hajos-Parrish-Eder-Sauer- Wiechert reaction.[1] cis-4,5-Methanoproline exhibits catalytic ability similar to proline (86% yield, 93% ee), whereas the trans-4,5- methanoproline is less selective (67% yield, 83% ee) and shows less acceleration. The reaction was also studied with hybrid density functional theory (B3LYP). The nearly planar cis-4,5-methanoproline amine better reflects the planar iminium of the transition states than the pyramidalized trans4,5-methanoproline. This difference in conformation is responsible for the observed higher enantioselectivity and enhanced catalytic behavior of the cis-4,5-methanoproline.
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.
Novel supported and unsupported prolinamides as organocatalysts for enantioselective cyclization of triketones
Pedrosa, Rafael,Andrés, José María,Manzano, Rubén,Pérez-López, César
supporting information, p. 3101 - 3104 (2013/06/27)
A novel prolylsulfonamide derived from ethylene diamine and its supported counterpart has been prepared and tested as enantioselective intramolecular aldol reaction of cyclic and acyclic triketones. Good to excellent yields and enantioselectivities have been obtained in water and under solvent free conditions.