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Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D‐HPLC
Author(s) -
Santi Micol,
Seitz Jakob,
Cicala Rossana,
Hardwick Tomas,
Ahmed Nisar,
Wirth Thomas
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904711
Subject(s) - chirality (physics) , electrochemistry , high performance liquid chromatography , flow (mathematics) , design of experiments , materials science , nanotechnology , analytical chemistry (journal) , chromatography , chemistry , computer science , electrode , physics , mechanics , mathematics , nuclear physics , statistics , chiral symmetry breaking , nambu–jona lasinio model , quark
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.