A new approach to α-(trifluoromethyl)benzyl substituted oxaziridines

• α-(Trifluoromethyl)benzyl substituted oxaziridines.
• Oxidation of 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols with m-CPBA led to CF3-functionalized oxaziridines.
• A similar procedure was applied for their trimethylsilyl protected derivatives.
• In all reactions studied, mixtures of diastereoisomers were formed.
• The prepared oxaziridines were shown to be able to oxidize thioanisole in the presence of methanesulfonic acid.

The synthesis of N-substituted oxaziridines bearing an α-(trifluoromethyl)benzyl substituent at C(3) was achieved by m-CPBA oxidation of the corresponding 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols and their trimethylsilyl protected derivatives, respectively. In all cases, mixtures of diastereoisomers were formed. The prepared oxaziridine derivatives were shown to be able to oxidize thioanisole to thioanisole S-oxide in the presence of methanesulfonic acid.

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