Project description
Harnessing enantioselective C-H oxidation in organic synthesis
Organic compounds are characterised by multiple and diverse bonds between carbon (C) and hydrogen (H). In metabolism, these C-H bonds can be converted into functional C-O bonds in a precise manner by oxidative enzymes, producing chiral metabolites of diverse structure and function. The EU-funded ECHO-GRACADE project aims to harness the power of enantioselective C-H oxidation in synthetic chemistry in the absence of real enzymes. For this purpose, scientists will employ small molecule manganese catalysts that will function as minimalistic hydroxylases. The project will focus on the design of these catalysts as tools in organic chemical synthesis for paradigmatic asymmetric reactions that involve C–H oxidation.
Objective
Chemo- and enantioselective oxidation of aliphatic C-H bonds is a cornerstone reaction in metabolism. The ubiquitous presence of multiple and diverse C-H bonds in organic molecules is used by oxidative enzymes to deliver functionality and chirality to metabolite precursors, rapidly creating product diversity. Despite its huge potential in organic synthesis, non-enzymatic enantioselective C-H oxidation of aliphatic sites remains inaccessible and has never been incorporated in synthesis. Harnessing the power of this reaction will open straightforward, yet currently inaccessible, paths in synthetic planning. However, realization of this goal requires conceptual breakthroughs in order to chemo-, regio- and stereo-selectively create a C-O bond from a non-activated alkyl C-H bond, even in the presence of a priori more reactive groups. In this project, chemo-, and site-selective asymmetric aliphatic oxidation is targeted by taking advantage of; a) stereoretentive enzyme-like metal-based C-H oxidations performed by small molecule manganese catalysts, devised as minimalistic hydroxylases, and b) polarity reversal exerted by fluorinated alcohol solvents in electron-rich functional groups, which enable chemoselective C-H hydroxylation of densely functionalized molecules. Desymmetrization via enantioselective C-H oxidation is devised as a powerful type of reaction that will create multiple chiral centers in a single step. Building on the rich chemical diversity and modular architecture of aminopyridine manganese complexes, rapid elaboration of libraries of catalysts is targeted. Rational manipulation of steric, electronic, directing effects and supramolecular substrate recognition factors guided by multiple parametrization analyses will be employed for directing evolution in catalyst design. This project will provide the catalysts and their use in paradigmatic reactions in order to establish enantioselective C-H oxidation as a reliable tool in organic synthesis.
Fields of science (EuroSciVoc)
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
- natural sciences chemical sciences electrochemistry electrolysis
- natural sciences chemical sciences organic chemistry alcohols
- natural sciences chemical sciences catalysis
- natural sciences biological sciences biochemistry biomolecules proteins enzymes
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Keywords
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Programme(s)
Multi-annual funding programmes that define the EU’s priorities for research and innovation.
Multi-annual funding programmes that define the EU’s priorities for research and innovation.
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H2020-EU.1.1. - EXCELLENT SCIENCE - European Research Council (ERC)
MAIN PROGRAMME
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Topic(s)
Calls for proposals are divided into topics. A topic defines a specific subject or area for which applicants can submit proposals. The description of a topic comprises its specific scope and the expected impact of the funded project.
Calls for proposals are divided into topics. A topic defines a specific subject or area for which applicants can submit proposals. The description of a topic comprises its specific scope and the expected impact of the funded project.
Funding Scheme
Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
ERC-ADG - Advanced Grant
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Call for proposal
Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.
Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.
(opens in new window) ERC-2019-ADG
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Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.
17004 GIRONA
Spain
The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.