What is it about?
Quaternary stereocenters are difficult to produce in a stereoselective way – especially if all substituents are attached to it via a carbon atom. In a recent publication in hashtag#ACSCatalysis Michael Friess in my lab at the Institute of Organic Chemistry at the Graz University of Technology could show in collaboration with with labs of Peter Macheroux (TU Graz) and Karl Gruber (University of Graz) that these motifs can be accessed in substituted cyclohexenones by the use of ene-reductase enzymes under environmentally benign conditions. https://lnkd.in/d_rbvgu8
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Why is it important?
Using wildtype enzymes and even cell lysates it is now possible to access an important class of functionalized chiral building blocks, which can be used as intermediates in total synthesis or the production of active pharmaceutical ingredients (API). Importantly, the used reaction conditions follow the principles of Green Chemistry and are environmentally benign.
Perspectives
We are delighted that this transformation gives access to interesting substrates with excellent enantioselectivities and might be of use for synthetic chemists in academia and industry.
Rolf Breinbauer
Technische Universitat Graz
Read the Original
This page is a summary of: Asymmetric Synthesis of Chiral 2-Cyclohexenones with Quaternary Stereocenters via Ene-Reductase Catalyzed Desymmetrization of 2,5-Cyclohexadienones, ACS Catalysis, April 2024, American Chemical Society (ACS),
DOI: 10.1021/acscatal.4c00276.
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