Abstract:
The direct asymmetric organocatalytic a-oxidation of aldehydes using trans-2-(p-methylphenylsulfonyl)-3-phenyloxaziridine is reported. This method affords the S isomer of alpha-hydroxy aldehydes, thereby complementing the selectivity for the R isomer observed using the two-step nitrosobenzene method. Use of alpha-methylproline and alpha-methylproline tetrazole significantly increases the enantioselectivity observedfor the alpha-oxidation of aldehydes compared to analogous unsubstituted organocatalysts.