| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313863 | Journal of Fluorine Chemistry | 2013 | 6 Pages |
•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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