In recent years 2-sulfonyl-and 2-sulfamyloxaziridines, la and lb, respectively, have received considerable attention as selective aprotic oxidizing reagents for a large variety of substrates. These reagents oxidize sulfides (selenides) to sulfoxides (selenoxides) without overoxidation.2,3 They selectively oxidize thiones to sulfines4 5and epoxidize alkenes.6 The aprotic nature of these reagents has made possible the facile syntheses of alcohols and phenols by hydroxylation of organometallic reagents,6 the oxidation of enolates to -hydroxy carbonyl compounds,7 and the synthesis of extremely acid-sensitive species such as -siloxy epoxides8 and sulfenic acids.9 Optically active 2-sulfonyl-and 2-sulfamyloxaziridines la,b afford the highest stereoselectivities reported for the oxidation of nonfunctionalized sulfides (up to 91% ee)1 and alkenes (up to 61% ee).5c The asymmetric oxidation of prochiral enolates to optically active -hydroxy carbonyl compounds (up to 95% ee) by (+)-and (-)-(camphorylsulfonyl)oxaziridines has recently been reported.10
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