Amino acid derivatives undergon on-Kolbe electrolysis to afford enantiomerically enriched a-alkoxyamino derivatives through intermediate chiralc arbenium ions. The products contain N,O-acetals which are important structural motifs foundi nb ioactive natural products.T he reactioni sp erformedi nacontinuous flow electrochemical reactor coupled to a2 D-HPLC for immediate online analysis. This allowed af ast screening of temperature, electrode material, current, flow-rate andc oncentration in aD oE approach. The combination with online HPLC demonstrates that also stereoselective reactions can benefit from ah ugely acceleratedo ptimisation by combining flow electrochemistry with multidimensional analysis.Scheme1.Electrochemical oxidation of N-arylcarbonylated amino acid derivativest oc hiral alkoxylated amides in aflow electro-microreactor.Scheme2.First example of 'memory of chirality' on N-aryl serine derivatives 1 reported by Matsumuraetal. [19] [a
The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste...
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