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

• α-(Aziridin-2-yl)-α-(trifluoromethyl)alcohols.
• Treatment of aziridin-2-yl ketones with (trifluoromethyl)trimethylsilane (CF3SiMe3) offers a convenient approach to α-(aziridin-2-yl)-α-(trifluoromethyl) alcohols.
• In the case of ethyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained and converted into the corresponding aziridinyl alcohols.

A convenient synthesis of α-(aziridin-2-yl)-α-(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 α-trifluoromethylated alcohols.

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