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 - Publikacja - MOST Wiedzy

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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

Abstrakt

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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Sławomir Makowiec, Ewelina Najda-Mocarska, Anna Zakaszewska, Karolina Janikowska. (2018). 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, 48(1), 14-25. https://doi.org/10.1080/00397911.2017.1383432

Pełna treść

Pełna treść dostępna od 2018-12-13

Informacje szczegółowe

Kategoria:
Publikacja w czasopiśmie
Typ:
artykuł w czasopiśmie wyróżnionym w JCR
Opublikowano w:
SYNTHETIC COMMUNICATIONS nr 48, strony 14 - 25,
ISSN: 0039-7911
Język:
angielski
Rok wydania:
2018
Opis bibliograficzny:
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
Źródła finansowania:
  • Foundation for Polish Science (POMOST/2013-8/6),

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