2-(Phenylsulfonyl)-3-phenyl-oxaziridine (Davis Reagent)

Introduction

In 1984, Davis and co-workers introduced a chiral derivative of N-sulfonyl oxaziridine[ ¹ ] as a versatile reagent for different organic functional group transformations; it is known as Davis reagent (Figure [1)].[ ² ]

Figure 1

The Davis reagent can be prepared by the biphasic basic oxidation of the N-benzylidene benzene-sulfonamide with MCPBA or oxone.[ ³ ] It is a neutral, aprotic, mild and stable colorless powder (mp 92–94 °C) and can be stored in ­amber-colored bottles at 5 °C.

Sulfonyloxaziridines share many characteristics with di­alkyldioxiranes and are widely used as versatile oxidizing reagents for the oxygenation of a variety of functional groups[ ⁴ ] such as sulfide (RSR) to sulfoxide (RSOR), disulfide (RSSR) to thiosulfinate (RSOSR), thiol (RSH) to sulfenic acid (RSOH) and selenide (RSeR) to selenoxide (RSeOR). Due to the stereoselective cleavage of the weak N–O bond and the chirality, the Davis reagent is significant for asymmetric functional group transformations.

• References

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