Electroreductive Access to 1,2-Aminoalcohols via Cross Aza-Pinacol Coupling of N‑Acyl Diarylketimines and Aldehydes
We present highly efficient and operationally simple synthetic methods for 1,2-aminoalcohols via electroreductive cross aza-pinacol coupling between N-acyl diarylketimines and aldehydes. Preliminary mechanistic studies including cyclic voltammetry and density functional theory (DFT) calculations sug...
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| Veröffentlicht in: | Organic letters 2024-04, Vol.26 (14), p.2733-2738 |
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| container_end_page | 2738 |
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| container_issue | 14 |
| container_start_page | 2733 |
| container_title | Organic letters |
| container_volume | 26 |
| creator | Kwak, Dongmin Jung, Sehwa Ha, Hyeonbin Han, Taedong Ryu, Do Hyun Kim, Hyunwoo Kwak, Jaesung |
| description | We present highly efficient and operationally simple synthetic methods for 1,2-aminoalcohols via electroreductive cross aza-pinacol coupling between N-acyl diarylketimines and aldehydes. Preliminary mechanistic studies including cyclic voltammetry and density functional theory (DFT) calculations suggest that the reaction is instigated by selective electrochemical single electron transfer (SET) of N-acylketimines. The developed electrochemical protocol is compatible to biorelevant functional groups, enabling late-stage functionalization of pharmacophores. |
| doi_str_mv | 10.1021/acs.orglett.3c01543 |
| format | Article |
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| ispartof | Organic letters, 2024-04, Vol.26 (14), p.2733-2738 |
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| source | American Chemical Society Journals |
| title | Electroreductive Access to 1,2-Aminoalcohols via Cross Aza-Pinacol Coupling of N‑Acyl Diarylketimines and Aldehydes |
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