期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 10, 页码 6347-6355出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00559
关键词
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资金
- University of Bologna
- MICINN [CTQ2016-75023-C2-2-P]
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.
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