Visible-Light-Activated Catalytic Enantioselective β‑Alkylation of α,β-Unsaturated 2‑Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs
An efficient and practical method for the enantioselective β-functionalization of α,β-unsaturated 2-acyl imidazoles is described. The method uses a previously devised chiral-at-metal rhodium catalyst (Λ-RhS, 4 mol %) along with Hantzsch ester derivatives as alkyl radical sources. The rhodium complex...
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| Veröffentlicht in: | Journal of organic chemistry 2018-09, Vol.83 (18), p.10922-10932 |
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| container_end_page | 10932 |
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| container_issue | 18 |
| container_start_page | 10922 |
| container_title | Journal of organic chemistry |
| container_volume | 83 |
| creator | de Assis, Francisco F Huang, Xiaoqiang Akiyama, Midori Pilli, Ronaldo A Meggers, Eric |
| description | An efficient and practical method for the enantioselective β-functionalization of α,β-unsaturated 2-acyl imidazoles is described. The method uses a previously devised chiral-at-metal rhodium catalyst (Λ-RhS, 4 mol %) along with Hantzsch ester derivatives as alkyl radical sources. The rhodium complex exerts a dual role as the visible-light-absorbing unit upon substrate binding and as the asymmetric catalyst. The method provides up to quantitative yields with excellent enantioselectivities up to 98% ee and can be classified as a redox-neutral, electron-transfer-catalyzed reaction. |
| doi_str_mv | 10.1021/acs.joc.8b01588 |
| format | Article |
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| title | Visible-Light-Activated Catalytic Enantioselective β‑Alkylation of α,β-Unsaturated 2‑Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs |
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