Study on Oxaziridine With Reference to Properties

Applications and Mechanisms of Oxaziridine in α-hydroxylation Reactions

Abstract

Oxaziridine are an important synthetic motif present inmany natural products. α-hydroxyketones have been synthesized in many ways,including reduction of α-diketones, substitution of a hydroxyl for a leavinggroup and direct oxidation of an enolate.Oxodiperoxymolybdenum(pyridine)-(hexamethylphosphoric triamide) (MoOPH) and N-sulfonyloxaziridines are the mostcommon electrophilic sources of oxygen implemented in this process. Oneadvantage of using N-sulfonyloxaziridinesis that higher chiral induction is almost invariably observed relative to MoOPHand other oxidants. High yield (77-91%) and dr (95:5 - 99:1) are reported for α-hydroxylation with theEvans' chiral auxiliary with N-sulfonyloxaziridineas the electrophile. Chiral induction has been demonstrated with many otherchiral ketones and ketones with chiral auxiliaries, including SAMP and RAMP.