Producing molecular complexity by means of cyclopropenimine-catalyzed cascade reactions

• Applicant: Dr. Fiene Horeischi
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2015 to 2016
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 283078719

For the upcoming research project the enantioselective BRØNSTED-base-catalyzed addition of C-H-acid carbonyl compounds to diverse Michael-acceptor molecules is to be developed. The 2,3-bis(dialkylamino)-substituted cyclopropenimines, which were found to be excellent organocatalysts in 1,4-Michael addition reactions by the group of Prof. Tristan H. Lambert, shall be used as promoters for these transformations. Following promising preliminary studies the cyclopropenimine-catalyzed reaction is to be refined. Beside comprehensive studies over the catalyst-activity there will be also an extension of the substrate scope. Until today only very acidic substrates can be used for these organocatalytic systems. The plan is to repeal this limitation and develop completely new reactivities of the cyclopropenimines. The second part of the project is to use the cyclopropenimines in more complex transformations. For this goal, starting compounds which contain a Michael acceptor functionality adjacent to a C-H-acid component are to be used as they are supposed to favor tandem reactions. Through cyclopropenimine-catalyzed Michael-Michael-sequences, synthetically interesting chiral compounds should be received. Looking further towards the responsible handling of valuable resources, the use of Lamberts cyclopropenimines in cascade reactions looks very desirable and therefore is going to be developed through optimizing processes.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Dr. Tristan H. Lambert, Ph.D.