Project description DEENESFRITPL Improved access to one of the most important pharmaceutical building blocks Carbon–hydrogen bonds are notoriously hard to break, yet pulling off hydrogens and replacing them with brand new entities is the stuff synthetic organic chemists' dreams are made of – and for good reason. Synthesising organic molecules, whether ones already present in nature or even ones that are not, is fundamental to applications in numerous fields from medicine and energy to organic electronics. The EU-funded DiPipe project is focussing on the functionalisation of piperidine, a widely used building block and chemical reagent for pharmaceuticals. Simplification of the reaction steps and processes will improve the transition-metal catalysed functionalisation of this important compound. Show the project objective Hide the project objective Objective The transition metal-catalyzed direct functionalization of C-H bonds is a major research topic across the world. However selective (regio-, enantio-, diastereoselective) and efficient functionalization of C(sp3)-H bonds, remains a significant challenge: C(sp3)-H bonds are omnipresent in organic molecules and their dissociation energies are large. The use of directing groups (DGs) “guiding” the metal to specific C-H bonds and allowing intramolecular C-H bond activation, is a recognized general approach to address the selectivity challenge. However, their installation and removal add steps to the overall reaction sequence. This proposal aims to develop unprecedented regio- and diastereoselective transition metal-catalyzed functionalization of piperidine derivatives with haloalkenes making use of transient DGs, installed and removed in situ during catalysis. Access to a large number of substituted piperidines as well as known and new bicyclic scaffolds can be achieved via post-functionalization of the vinylpiperidine reaction products, making the aimed synthetic methodology potentially suitable for molecular library synthesis in drug discovery. A particularly challenging objective of the proposal is the remote (meta) functionalization with respect to the DG at C3 of the piperidine ring. Piperidine is chosen as a central heterocycle core in this application based on its importance in drug design and wide occurrence in commercial drugs (privileged scaffold). Fields of science medical and health sciencesbasic medicinepharmacology and pharmacydrug discoverymedical and health sciencesbasic medicinemedicinal chemistrynatural scienceschemical sciencescatalysis Programme(s) H2020-EU.1.3. - EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions Main Programme H2020-EU.1.3.2. - Nurturing excellence by means of cross-border and cross-sector mobility Topic(s) MSCA-IF-2018 - Individual Fellowships Call for proposal H2020-MSCA-IF-2018 See other projects for this call Funding Scheme MSCA-IF-EF-ST - Standard EF Coordinator UNIVERSITEIT ANTWERPEN Net EU contribution € 178 320,00 Address PRINSSTRAAT 13 2000 Antwerpen Belgium See on map Region Vlaams Gewest Prov. Antwerpen Arr. Antwerpen Activity type Higher or Secondary Education Establishments Links Contact the organisation Opens in new window Website Opens in new window Participation in EU R&I programmes Opens in new window HORIZON collaboration network Opens in new window Total cost € 178 320,00
