H2020Индивидуална стипендия2019–2021

DiPipe · Direct remote C-H functionalization in piperidine derivatives

„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“

Период: 2019-04-01 → 2021-03-31
Финансиране от ЕС: 178 320 €
Участници: 1
Схема: MSCA-IF-EF-ST

Линиите свързват координатора с партньорите.

Накратко на български

Химиците разработват методи за прецизно променяне на връзките в пиперидин и циклохексан чрез добавяне на халоалкени. Това помага за по-бързото създаване на нови молекулярни структури, които се използват при разработването на лекарства.

Този кратък обзор е генериран от изкуствен интелект

Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.

Резултати накратко

Direct remote C-H functionalization in piperidine derivatives

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 bond 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 project aims to develop unprecedented regio- and diastereoselective transition metal catalyzed functionalization of cyclohexyl and piperidine derivatives with haloalkenes making use of transient DGs and already installed DGs. 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 project is the remote (meta) functionalization with respect to the DG at C3 of the piperidine ring. Piperidine is chosen as a central heterocycle core based on its importance in drug design and wide occurrence in commercial drugs (privileged scaffold).

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз

Цел на проекта

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).

Оригинален текст от CORDIS (на английски).

Участници

UNIVERSITEIT ANTWERPEN · AntwerpenКоординаторБелгия