CORDIS
EU research results

CORDIS

English EN

Direct remote C-H functionalization in piperidine derivatives

Project information

Grant agreement ID: 837718

Status

Ongoing project

  • Start date

    1 April 2019

  • End date

    31 March 2021

Funded under:

H2020-EU.1.3.2.

  • Overall budget:

    € 178 320

  • EU contribution

    € 178 320

Coordinated by:

UNIVERSITEIT ANTWERPEN

Belgium

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).
Leaflet | Map data © OpenStreetMap contributors, Credit: EC-GISCO, © EuroGeographics for the administrative boundaries

Coordinator

UNIVERSITEIT ANTWERPEN

Address

Prinsstraat 13
2000 Antwerpen

Belgium

Activity type

Higher or Secondary Education Establishments

EU Contribution

€ 178 320

Project information

Grant agreement ID: 837718

Status

Ongoing project

  • Start date

    1 April 2019

  • End date

    31 March 2021

Funded under:

H2020-EU.1.3.2.

  • Overall budget:

    € 178 320

  • EU contribution

    € 178 320

Coordinated by:

UNIVERSITEIT ANTWERPEN

Belgium