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.

Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates / Cerveri, Alessandro; Nieto Faza, Olalla; Lopez Silva, Carlos; Grilli, Stefano; Monari, Magda; Bandini, Marco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1520-6904. - 84:10(2019), pp. 6347-6355. [10.1021/acs.joc.9b00559]

Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates

Alessandro Cerveri;
2019-01-01

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.
2019
Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates / Cerveri, Alessandro; Nieto Faza, Olalla; Lopez Silva, Carlos; Grilli, Stefano; Monari, Magda; Bandini, Marco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1520-6904. - 84:10(2019), pp. 6347-6355. [10.1021/acs.joc.9b00559]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/3044219
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