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Published on: August 18, 2017
Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D-HPLC
Micol Santi1, Jakob Seitz1, Rossana Cicala1
1School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Abstract:
Amino acid derivatives undergo non-Kolbe electrolysis to afford enantiomerically enriched α-alkoxyamino derivatives through intermediate chiral carbenium ions. The products contain N,O-acetals which are important structural motifs found in bioactive natural products. The reaction is performed in a continuous flow electrochemical reactor coupled to a 2D-HPLC for immediate online analysis. This allowed a fast screening of temperature, electrode material, current, flow-rate and concentration in a DoE approach. The combination with online HPLC demonstrates that also stereoselective reactions can benefit from a hugely accelerated optimisation by combining flow electrochemistry with multidimensional analysis.
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