Photocatalyzed enantiodivergent synthesis of homoallylic and carboxylic acids featuring heterodiaryl quaternary carbon stereocenters

Project Information

PEACE

Grant agreement ID: 101105057

DOI

10.3030/101105057

Project terminated on 31 January 2024

EC signature date 12 April 2023

Start date 1 October 2023

End date 30 September 2025

Funded under

• Marie Skłodowska-Curie Actions (MSCA)

Total cost

No data

EU contribution

€ 165 312,96

Coordinated by

FUNDACIO INSTITUT CATALA D'INVESTIGACIO QUIMICA
Spain

Periodic Reporting for period 1 - PEACE (Photocatalyzed enantiodivergent synthesis of homoallylic and carboxylic acids featuring heterodiaryl quaternary carbon stereocenters)

Reporting period: 2023-10-01 to 2025-09-30

Summary of the context and overall objectives of the project

The PEACE project sought to tackle novel research and innovation (R&I) methods for creating diaryl all-carbon quaternary carbon centers through a pioneering photocatalyzed enantiodivergent approach. By utilizing a single chiral catalytic system, the project aimed to significantly reduce the methodology's costs. This involved devising substrate-based enantiodivergent strategies, relying on carefully chosen reaction partners to revolutionize the synthesis of both enantiomers of stereocenters encompassing diaryl quaternary carbon centers.
Specifically, the outcomes, results, and impacts of PEACE were expected to manifest in several dimensions: (a) Scientific Impact: PEACE aimed to expand knowledge in sustainable catalytic synthesis of all-carbon stereocenters, paving the way for new scientific approaches adaptable and scalable in both academic and industrial settings. This effort aimed to bolster investment in green R&I while educating researchers, both young and seasoned, on novel catalytic and sustainable processes. (b) Economic/Technological/Societal Impact: Furthermore, the project's outcomes aimed to address the pressing demand for a more sustainable future in high-value fine-chemical production. Designing innovative and economically sustainable approaches to quaternary stereocenters posed a significant challenge in the fine chemical industry. PEACE aimed to impact this sector by developing and designing a new divergent synthesis utilizing a single catalytic system, thus promoting a greener future. With a focus on medicinal chemistry, this project was poised to significantly decrease the overall synthesis costs of Active Pharmaceutical Ingredients (APIs).

Work performed from the beginning of the project to the end of the period covered by the report and main results achieved so far

During the four months of the PEACE project, a new family of 1,4-dihydropyridines (DHP) as aryl radical precursors have been synthetized through a new reaction sequence. At the same time, a family of well-known vinyl cyclic carbonates (VCC) were also prepared. Furthermore, initial screening of the reaction conditions toward the generation of new diaryl all-carbon quaternary carbon centers were performed. Challenges associated to the dual metal-photoredox enantiodivergent catalysis approach have been faced and promising preliminary results were achieved.

Progress beyond the state of the art and expected potential impact (including the socio-economic impact and the wider societal implications of the project so far)

Not applicable due to early termination and short implementation period (4 months)

Photocatalyzed synthesis