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Direct remote C-H functionalization in piperidine derivatives

Direct remote C-H functionalization in piperidine derivatives

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).

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