Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols

作者：Mloston Grzegorz^*; Obijalska Emilia; Ziebacz Paulina; Matyszewski Krzysztof; Urbaniak Katarzyna; Linden Anthony; Heimgartner Heinz

来源：Journal of Fluorine Chemistry, 2013, 156: 192-197.

DOI：10.1016/j.jfluchem.2013.09.011

• Aziridines
• Aziridinyl ketones
• Aziridinyl alcohols
• (Trifluoromethyl)trimethylsilane
• Nucleophilic trifluoromethylation

A convenient synthesis of alpha-(aziridin-2-yl)-alpha-(trifluoromethyl) alcohols starting with ethyl aziridine-2-carboxylates is reported. Grignard reaction with the corresponding Weinreb amides led to aziridin-2-yl ketones, and subsequent treatment with Ruppert-Prakash reagent gave the trimethylsilylated target compounds as mixtures of diastereoisomers, which were desilylated with TBAF. In the case of ethyl 1((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained, separated chromatographically and transformed into the desired enantiomerically pure alpha-trifluoromethylated alcohols.

• 出版日期2013-12