Chemistry

Chemists develop metal-free method to selectively convert symmetric diols into one of two enantiomers

Internal view of the photoreactor setup in operation. Credit: Science (2024). DOI: 10.1126/science.adq8029

A team of chemists at the University of Cambridge has developed a metal-free method to selectively convert symmetric diols into one of their two enantiomers. In a paper published in the journal Science, the research group exploits the ability of the chiral form of quinuclidine (quinuclidine is derived from cinchona alkaloids) to catalyze the solution memory of mesodiol under blue light in conjunction with a photocatalyst. Hydrogen atoms were extracted. From symmetrical molecules.

Noting that the transfer of hydrogen atoms between molecules is a fundamental task in modern chemistry, the research team proposed enantioselective hydrogen production in which one of the enantiomers of a chiral product is preferentially produced during a chemical reaction. We considered making the process more selective by adding atomic transfers.

Their research included the development of a new method for enantioselective hydrogen atom extraction, one that allows the introduction of chirality into the process. By using a catalyst derived from the cinchona alkaloid family, they were able to take advantage of the resulting chiral amine structure to selectively remove hydrogen atoms from specific carbon centers of mesodiol.

They achieved this by focusing on the use of chiral quinuclidine compounds derived from cinchona alkaloids, which allowed them to catalyze the desymmetrization of mesodiols with blue light and photocatalysis.

The method used by the researchers enabled selective epimerization, converting one stereoisomer into another by replacing hydrogen atoms with thiols. Initially, this catalyst was made by direct hydrogenation of cinchona alkaloids, but the reactivity and selectivity were not as high as expected.

However, further studies showed that changing the hydroxyl group to a protected amine and reversing the stereocenter could significantly improve the performance of the catalyst.

The researchers point to their work as a proof of principle, noting that in some parts of their technique quinuclidine can be swapped out and a chiral version used instead. They also point out that the catalyst could be used in site-selective chemistry if desired. They conclude by suggesting that their work may have important implications for pharmaceutical applications and perhaps other research efforts as well.

Further information: Antti SK Lahdenperä et al., Chiral hydrogen atom abstraction catalyst for enantioselective epimerization of meso-diols, Science (2024). DOI: 10.1126/science.adq8029

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Citation: Chemists develop metal-free method to selectively convert symmetric diols into one of two enantiomers (October 25, 2024) https://phys.org/news/2024-10 Retrieved October 25, 2024 from -chemists-metal-free-symmetric-diols.html

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