An electrochemical method for the green and practical
synthesis of a broad range of substituted isoxazoline cores is presented. Both
aryl and more challenging alkyl aldoximes are converted to the desired
isoxazoline <i>via</i> an electrochemically
enabled regio- and diastereoselective reaction with electron-deficient alkenes.
Additionally, <i>in-situ</i> reaction
monitoring methods compatible with electrochemistry equipment have also been
developed in order to probe the reaction pathway. Supporting analyses from
kinetic (time-course) modeling and density functional theory support a
stepwise, radical-mediated mechanism, and discounts hypothesized involvement of
closed shell [3+2] cycloaddition pathways.