New bifunctional carbohydrate-like thiourea derivatives – design and first application in organocatalysis

Autor:	Tommaso Pecchioli, Reinhold Zimmer, Luise Schefzig, Hans-Ulrich Reissig, Lutz Adam
Rok vydání:	2018
Předmět:	Trifluoromethyl 010405 organic chemistry Phenyl isothiocyanate Organic Chemistry Carbohydrate 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Oxepane Thiourea chemistry Pyran Organocatalysis Organic chemistry Bifunctional
Zdroj:	Synthetic Communications. 48:1945-1956
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397911.2018.1468465
Popis:	From easily available aminopyran and aminooxepane derivatives and 2,5-bis(trifluoromethyl)phenyl isothiocyanate the corresponding thiourea derivatives were prepared. One compound was further modified by introducing a tertiary amino group. The four catalysts were then examined as catalysts in a Michael addition of acetylacetone to β-nitrostyrene. A 1:1 mixture of one of these thioureas with an (S)-prolinol derivative was also tested as catalyst, but no synergetic effect was found. The best yield achieved was 88% and the highest ee amounted to 39%. In a preliminary experiment, the aldol reaction of acetone with isatin was investigated. One catalyst provided the expected aldol product in low yield, but in excellent enantioselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::611f691d5d6c4f5568e1114075def72d https://doi.org/10.1080/00397911.2018.1468465 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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