The first example of an
exo-camphorylsulfonyloxaziridine 4a was prepared
by m-CPBA oxidation
of camphor imine 9. This surprising result is due to
the conformation of the imine which apparently
prevents attack of the peracid from the endo direction. Similar
oxidations of all other camphorsulfonylimines result in the endo-oxaziridine exclusively.
Asymmetric oxidation of sulfides to
sulfoxides and the α-hydroxylation of enolates by 4 can be
interpreted in terms of open transition
states where nonbonded interactions are minimized. These results
support earlier conclusions and
predictions of the stereoselectivity and mechanisms of molecular
recognition by the N-sulfonyloxaziridine class of oxidizing reagents.
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