L-cysteine-functionalized CuPt: A chiral electrode for the asymmetric electroreduction of aromatic ketones

Enantioselective recognition, synthesis, and separation of pharmaceutical compounds at chiral metallic surfaces

“…[49] CuPt was recently also modified with L-Cys for the enantioselective reduction of 2,2,2-trifluroacetophenone with moderate ee%. [50] The pharmaceutical applications of new heterogeneous chiral metal phases should be further studied to illustrate the potential of these surfaces for pharmaceutical applications. Therefore, further studies are needed, especially concerning a) the versatility of the catalysts for other types of asymmetric reactions such as alkylation, [51] acylation, [52] or carboxylation, [53] which are carried out for the synthesis of various pharmaceutical products such as penicillamine, ibuprofen, or naproxen, respectively; b) their long-term stability, for example, creating the stable chiral encoded alloys; [16j] c) improvving the production rate and %ee by optimizing the mass transport, either by improving diffusion limitations at the chiral mesoporous metal surfaces based on several techniques, such as multi-metal electrohydrodynamic redox 3D printing [54] or the synergy with magnetic fields; [55] d) cost reduction by using nonnoble metals or their alloys.…”

“…For example, Cu nanorods were modified with L‐Cys, [48] which was electropolymerized on immobilized AuNPs for chiral recognition of amino acids [49] . CuPt was recently also modified with L‐Cys for the enantioselective reduction of 2,2,2‐trifluroacetophenone with moderate ee% [50] . The pharmaceutical applications of new heterogeneous chiral metal phases should be further studied to illustrate the potential of these surfaces for pharmaceutical applications.…”

Recent Advances in Chiral Electrodes for Asymmetric Electrosynthesis

“…Recently, (R)-α-(trifluoromethyl)benzyl alcohol with the yield of 73 % and an ee value of 43 % was synthesized by asymmetric electroreduction of 2,2,2-trifluoroacetophenone on the L-cysteine-CuPt cathode (Table 1 entry 5). [14] The same approach can be used to prepare L-cysteine-Cu, L-cysteine-Pt, L-cysteine-PdPt and L-cysteine-FePt. The stereoselectivity of these chiral modified electrodes is slightly different due to the difference in L-cysteine loading.…”

Electrochemically Promoted Asymmetric Transfer Hydrogenation of 2,2,2-Trifluoroacetophenone

“…9,10 There have been many reports on the asymmetric electrosynthesis of chiral alcohols from aromatic ketones, starting from the perspectives of chiral media 11 and chiral inducers. 12,13 In our previous work, chirally functionalized electrodes, such as alkaloid@metal composites, 14,15 L-cysteine-functionalized CuPt alloy, 16 and mino acid-functionalized multiwalled carbon nanotubes, 17,18 have been prepared, and the ee value has been increased to 40−70%. Although the performance of the target asymmetric reaction can be greatly improved by fixing the chiral inducer on the surface of the electrode, its reactivity is still not comparable to homogeneous chiral transition metal complexes.…”

“…Recently, due to its mild reaction conditions, low energy consumption, and easy control of the reaction process, more and more research studies on electroorganic synthesis have been reported , and reviewed. , Among them, asymmetric electrosynthesis has attracted great attention, in view of the particularity of chiral products. , There have been many reports on the asymmetric electrosynthesis of chiral alcohols from aromatic ketones, starting from the perspectives of chiral media and chiral inducers. , In our previous work, chirally functionalized electrodes, such as alkaloid@metal composites, , l -cysteine-functionalized CuPt alloy, and mino acid-functionalized multiwalled carbon nanotubes, , have been prepared, and the ee value has been increased to 40–70%. Although the performance of the target asymmetric reaction can be greatly improved by fixing the chiral inducer on the surface of the electrode, its reactivity is still not comparable to homogeneous chiral transition metal complexes.…”