High‐Pressure‐Mediated Asymmetric Organocatalytic Hydroxyalkylation of Indoles with Trifluoromethyl Ketones. Issue 18 (31st August 2016)

• Record Type: Journal Article
• Authors: Kasztelan, Adrian; Biedrzycki, Michał; Kwiatkowski, Piotr
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 18(2016)
• Page Start: 2962
• Page End: 2969
• Publication Date: 2016-08-31
• Subjects: asymmetric organocatalysis -- Cinchona alkaloids -- Friedel–Crafts reaction -- high-pressure effect -- indoles -- trifluoromethyl group; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600327
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :