Research by RWTH Chemists Published in Nature

23/09/2019

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The world-leading science journal Nature has published a paper by a research team headed by Professor Franziska Schoenebeck.

 

Earlier this year, Professor Franziska Schoenebeck, Chair of Organic Chemistry I, and her team published an article on stereochemically-defined olefins in the prestigious journal Science. In September 2019, under the title "Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas," the scientists present their current research on the importance of amides and related carbonyl derivatives in the natural and biosciences in the internationally esteemed science journal Nature.

The article "E-Olefins through intramolecular radical relocation" was published in Science on January 25, 2019. It is concerned with research on gaining control over the selectivity of carbon-carbon double bond migration. These provide access to stereochemically defined olefins for pharmaceuticals, food, fragrances, materials, and petrochemical products. Control of the geometry of carbon-carbon double bonds plays an important role in chemical manufacturing. A useful trick here is to shift hydrogen atoms around to selectively interconvert double bond isomers. However, this approach typically requires precious metals.

In their latest publication, the RWTH chemists report a method to synthesize highly relevant carbonyl derivatives and amides. As a key biological building block, the stability and conformation of amides affect the structures of peptides and proteins as well as their biological function. In addition, amide-bond formation is one of the most frequently used chemical transformations. Given their ubiquity, a technology that is capable of modifying the fundamental properties of amides without compromising on stability may have considerable potential in pharmaceutical, agrochemical and materials science. In order to influence the physical properties of organic molecules such as solubility, lipophilicity, and stability and to increase bioactivity and cellular permeability, researchers typically utilize modifications with isosteres or N-methylation.

Schoenebeck’s team has developed a straightforward method to access N-trifluoromethyl analogues of amides and related carbonyl compounds. The method relies on the preparation of bench-stable carbamoyl fluoride building blocks, which can be readily diversified to the corresponding N–CF3 amides, carbamates, thiocarbamates, and ureas. It has been observed that N-CF3 amides are more stable than their naturally occurring analogues or Me derivatives. The method tolerates rich functionality and stereochemistry, so that it can be used for highly functionalized compounds, including analogues of widely used drugs, antibiotics, hormones and polymer units.

The research articles are available via the following links:

E-Olefins through intramolecular radical relocation

Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas