2018-009 – Second Generation Chiral Poly-N-vinylpyrrolidinones

Researchers at Kansas State University have discovered a new class of polymers, namely chiral-substituted poly-N-vinylpyrrolidinones (CSPVPs), that can help produce improved, more effective versions of existing chemicals and pharmaceuticals: Selective Oxidation of Natural Products:Currently, 59% of all industrial pharmaceuticals are derivatives of bioactive natural products (NPs). These CSPVPs have the ability to stabilize bimetallic nanoclusters and oxidize these NPs regio- and stereo-selectively using hydrogen peroxide as an oxidant: The newly installed ketone (or hydroxyl) group can be converted into various functionalities such as hydroxyl, carbonyl, amine, amide, and sulfide, which may enhance pharmacological properties such as pharmacokinetics and bioactivity of these NPs. Late-stage aliphatic C-H oxidation, C-H azidation, and C-H chlorination of complex molecules has been the highlight of synthetic organic chemistry in recent years. These CSPVPs helps produce a number of synthetic intermediates for possible structural modification in improving or altering pharmacological or biological properties. Some of these chiral oxidized molecules are difficult to obtain by other methods. Enantioselective Oxidation of Alkenes and Cycloalkanes:Acyclic and cyclic alkenes are oxidized by the chiral bimetallic nanocluster-CSPVP-O2 to give syn-dihydroxylated products, similar to that from the Sharpless asymmetric dihydroxylation reaction, but using Pd/Au nanoclusters and not-toxic osmium metal. Cycloalkanes were also enantioselectively oxidized by using Cu/Au-CSPVP and hydrogen peroxide. Aarushi Gupta-Sheth aarushi@ksu.edu 785-532-3907

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