Synthesis of the 3- and 5-Benzyl-Aca Linkers

Racemic 3-benzylcyclohexanone is the precursor in this stereoselective synthesis of spirocyclic oxaziridines.  It is condensed with (R)-a-methylbenzylamine which is oxidized with a bulky oxidizing agent such as monoperoxycamphoric acid to yield a mixture of primarily two oxaziridines.


The formation of oxaziridines is a stereoselective process explained by the equatorial approach of the oxidizing agent toward the imine thus producing the stereoisomeric adducts.

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Mechanistic Issues