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Memory of chirality in flow electrochemistry: fast optimisation with DoE and online 2D-HPLC

Santi, Micol, Seitz, Jakob, Cicala, Rossana, Hardwick, Tomas, Ahmed, Nisar and Wirth, Thomas 2019. Memory of chirality in flow electrochemistry: fast optimisation with DoE and online 2D-HPLC. Chemistry - A European Journal 25 (71) , pp. 16230-16235. 10.1002/chem.201904711
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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 0947-6539
Funders: School of Chemistry, Cardiff University, the EU and the Welsh Government for a Marie Sk�odowska�Curie Cofund grant (No 663830).
Date of First Compliant Deposit: 29 November 2019
Date of Acceptance: 5 November 2019
Last Modified: 29 Jun 2020 15:08
URI: http://orca.cf.ac.uk/id/eprint/127244

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