Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D‐HPLC | Zendy

Santi Micol | Zendy; Seitz Jakob | Zendy; Cicala Rossana | Zendy; Hardwick Tomas | Zendy; Ahmed Nisar | Zendy; Wirth Thomas | Zendy

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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 , flow (mathematics) , materials science , high performance liquid chromatography , nanotechnology , computer science , chemistry , chromatography , physics , mechanics , nuclear physics , electrode , 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.

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