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New thiourea organocatalysts and their application for the synthesis of 5-(1H-indol-3-yl)methyl-2,2-dimethyl-1,3-dioxane-4,6-diones a source of chiral 3-indoylmethyl ketenes
Abstract
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
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
SYNTHETIC COMMUNICATIONS
no. 48,
pages 14 - 25,
ISSN: 0039-7911 - Language:
- English
- Publication year:
- 2018
- Bibliographic description:
- Makowiec S., Najda-Mocarska E., Zakaszewska A., Janikowska K.: New thiourea organocatalysts and their application for the synthesis of 5-(1H-indol-3-yl)methyl-2,2-dimethyl-1,3-dioxane-4,6-diones a source of chiral 3-indoylmethyl ketenes// SYNTHETIC COMMUNICATIONS. -Vol. 48, nr. 1 (2018), s.14-25
- DOI:
- Digital Object Identifier (open in new tab) 10.1080/00397911.2017.1383432
- Sources of funding:
-
- Foundation for Polish Science (POMOST/2013-8/6),
- Verified by:
- Gdańsk University of Technology
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