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Photochemical Desymmetrization for Stereoselective C(sp³)-H Functionalization via HAT Catalysis

Project description

Highly efficient and selective chiral molecules

In chemistry, chiral molecules are mirror images that cannot be superimposed. These structures are vital in pharmaceuticals, where the right- or left-handed version of a molecule can have drastically different effects. With the support of the Marie Skłodowska-Curie Actions programme, the DESY-HAT project will create chiral molecules from simple, abundant starting materials by modifying carbon-hydrogen (C–H) bonds – the most common bonds in organic molecules. Researchers will use visible light and a process called hydrogen atom transfer (HAT) to selectively transform symmetrical compounds into complex chiral products. By combining HAT with enantioselective organocatalysis (a method to control molecular shape), DESY-HAT aims to develop sustainable techniques for producing biologically important compounds.

Objective

A pressing challenge in synthetic chemistry is developing sustainable methods to convert abundant feedstocks into valuable chiral products. The DESY-HAT project addresses this by pioneering new catalytic techniques, powered by visible light, to achieve stereoselective functionalization of carbon–hydrogen (C–H) bonds, the most ubiquitous moiety in organic molecules. Specifically, the project aims to access complex chiral molecules directly from readily available C–H substrates, including natural products, through enantioselective C–H functionalization via Hydrogen Atom Transfer (HAT) processes. The DESY-HAT project focuses on using HAT to selectively target C(sp³)–H bonds in symmetrical and meso substrates. The resulting desymmetrization processes will provide direct access to highly enantioenriched chiral products. This innovative approach, combining HAT with enantioselective organocatalysis, is a largely unexplored frontier in the field. The project will develop HAT desymmetrization strategies and apply them for enantioselective C(sp³)–C(sp³) and C(sp³)–heteroatom bond formation.

The project benefits from the Melchiorre group’s expertise in radical photochemistry and organocatalysis and will receive industrial guidance from Bayer AG Pharmaceuticals to identify suitable C–H substrates and assist with scaling up processes to practical applications. Through this interdisciplinary research, DESY-HAT will generate chiral compounds with biologically relevant frameworks, advancing the field of asymmetric synthesis while providing me with crucial skills for the next stage of my career.

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Topic(s)

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HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships

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Call for proposal

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(opens in new window) HORIZON-MSCA-2024-PF-01

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Coordinator

ALMA MATER STUDIORUM - UNIVERSITA DI BOLOGNA
Net EU contribution

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.

€ 193 643,28
Address
VIA ZAMBONI 33
40126 Bologna
Italy

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Region
Nord-Est Emilia-Romagna Bologna
Activity type
Higher or Secondary Education Establishments
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Total cost

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.

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