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EnglishThe stereoselective phosphine-catalyzed ((pMeOC(6)H(4))(3)P, 10-20 mol %) dearomatization of 3-NO2-indoles with allenoates is described. A range of densely functionalized indolines (18 examples) is obtained in high yields (up to 96%) under mild reaction conditions (rt, air, reagent-grade solvent). Computational simulations and labeling experiments revealed a stepwise [3 + 2]-type mechanism involving a water-assisted hydrogen shift and accounted for the diastereoselection recorded.
| Titolo: | Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates |
| Autore/i: | Alessandro Cerveri; Olalla Nieto Faza; Carlos Lopez Silva; Stefano Grilli; Magda Monari; Marco Bandini |
| Autore/i Unibo: | |
| Anno: | 2019 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.joc.9b00559 |
| Abstract: | The stereoselective phosphine-catalyzed ((pMeOC(6)H(4))(3)P, 10-20 mol %) dearomatization of 3-NO2-indoles with allenoates is described. A range of densely functionalized indolines (18 examples) is obtained in high yields (up to 96%) under mild reaction conditions (rt, air, reagent-grade solvent). Computational simulations and labeling experiments revealed a stepwise [3 + 2]-type mechanism involving a water-assisted hydrogen shift and accounted for the diastereoselection recorded. |
| Data stato definitivo: | 2020-02-22T08:52:35Z |
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