期刊
SYNTHETIC COMMUNICATIONS
卷 48, 期 1, 页码 14-25出版社
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2017.1383432
关键词
1,3-Dioxane-4,6-dione; alkylation; heteroaromatic; Meldrum's acid; thoiurea organocatalyst
资金
- European Union under the European Regional Development Fund [POMOST/2013-8/6]
The stereoselective properties of modified thiourea organocatalysts were tested in the Friedel-Crafts alkylation of indole with 5-arylidene-2,2-dimethyl-1,3-dioxane-4,6-diones, which produces chiral 5-((1H-indol-3-yl)(aryl) methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones. Based on a tentative reaction mechanism for ((S)-N-benzyl-2-(3-(3,5-bis (trifluoromethyl) phenyl) thioureido)-N, 3,3-trimethylbutanamide organocatalysts, modifications were applied in four selected regions. Systematic structure-stereoselectivity relationship study allowed designing the best efficient organocatalyst for the investigated Friedel-Crafts alkylation of indole with 5-arylidene-2,2-dimethyl-1, 3-dioxane-4,6-diones. [GRAPHICS] .
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