High-Pressure-Mediated Asymmetric Organocatalytic Hydroxyalkylation of Indoles with Trifluoromethyl Ketones

An enantioselective hydroxyalkylation of indoles and 7‐azaindole with trifluoromethyl ketones was found to be effectively promoted under high‐pressure conditions with a low loading of Cinchona alkaloids (e.g., 1–3 mol% of cinchonidine). Chiral tertiary alcohols containing a trifluoromethyl group wer...

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Veröffentlicht in:Advanced synthesis & catalysis 2016-09, Vol.358 (18), p.2962-2969
Hauptverfasser: Kasztelan, Adrian, Biedrzycki, Michał, Kwiatkowski, Piotr
Format: Artikel
Sprache:eng
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Zusammenfassung:An enantioselective hydroxyalkylation of indoles and 7‐azaindole with trifluoromethyl ketones was found to be effectively promoted under high‐pressure conditions with a low loading of Cinchona alkaloids (e.g., 1–3 mol% of cinchonidine). Chiral tertiary alcohols containing a trifluoromethyl group were obtained at 9 kbar with good yield and enantioselectivity up to 89%, whereas usually merely traces of products were detected at atmospheric pressure.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600327