Z-Stereoretentive
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The Z-alkene geometry is prevalent in various chemical compounds, including numerous building blocks, fine chemicals, and natural products. Unfortunately, established Mo, W, and Ru Z-selective catalysts lose their selectivity at high temperatures required for industrial processes like macrocyclic musk production via reactive distillation, which limits their synthetic applications. To address this issue, we developed a catalyst capable of providing Z-alkenes with high selectivity under harsh conditions.
Our research revealed a novel dithiolate ligand that, stabilised by resonance, delivers high selectivity at temperatures up to 150 °C in concentrated mixtures. This distinguishes the dithioquinoxaline complex from existing Z-selective catalysts. Notably, this unique trait does not compromise the new catalyst’s usability under classical conditions, matching the activity of known stereoretentive catalysts. Furthermore, the new quinoxaline-based catalyst enables the valorisation of bio-sourced alkene feedstocks and the production of agricultural sex pheromones for pest control.
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![Diagram illustrating the use case of the Z-Stereoretentive catalyst in the production of active pharmaceutical ingredients (APIs). The catalyst (Cat) is used at 0.5 mol% under room temperature (RT) for 4 hours in tetrahydrofuran (THF) to achieve high Z-selectivity (Z/E = 99:1) with an 85% isolated yield. The reaction involves an alkyl substrate (R = H, alkyl) and results in a Z-selective product. The bottom part of the diagram shows the chemical structure of a Baricitinib API analogue produced using this method, highlighting the efficiency and high selectivity of the Z-Stereoretentive catalyst even at high temperatures. This application demonstrates the catalyst's suitability for pharmaceutical manufacturing, ensuring high yields and precise selectivity in API synthesis.]( "Use Case of Z-Stereoretentive Catalyst in API Production")
![Diagram illustrating the use of Z-Stereoretentive catalyst in the production of fine chemicals from renewable feedstocks. The top reaction shows the conversion of an alkyl substrate using 1 mol% catalyst at room temperature (RT) for 2 hours under neat conditions at 10 mbar, achieving a 68% yield and a Z/E ratio of 99:1, resulting in a musky fruity compound. The middle reaction demonstrates the conversion of methyl oleate (Z/E = 99:1) using 0.1 mol% catalyst in THF at RT for 1 hour, achieving 50% conversion at equilibrium. The bottom reaction shows the conversion of oleic acid (Z/E = 99:1) using 0.25 mol% catalyst in hexane at RT for 1 hour, also achieving 50% conversion at equilibrium. These reactions highlight the catalyst's high Z-selectivity, efficiency, and suitability for producing valuable fine chemicals from renewable sources.]( "Z-Stereoretentive Catalyst in Fine Chemicals Production from Renewable Feedstocks")
