American Chemical Society
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A New General Method for the Preparation of N-Sulfonyloxaziridines

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journal contribution
posted on 2005-11-24, 00:00 authored by José Luis García Ruano, José Alemán, Cristina Fajardo, Alejandro Parra
A simple procedure to obtain N-alkylsulfonyl- and N-arylsulfonyloxaziridines from the corresponding N-sulfinylimines involving a one-pot, two-step oxidation process with m-CPBA (1 equiv) and m-CPBA/KOH (1.1 equiv) is reported. The method is applicable to N-sulfinylimines derived from aldehydes (aliphatic and aromatic) and ketones (dialkyl and aryl alkyl) and preserves CC-conjugated double bonds. Almost quantitative yields, very mild conditions (usually less than 5 min at room temperature), and easy purification by filtration are the main features of this new procedure, which can be performed at a gram scale.