Catalytic asymmetric aminohydroxylation of olefins with sulfonamides

An improved method for converting an olefinic substrate to an asymmetric hydroxylamine product by asymmetric addition of a nitrogen source and a hydroxyl radical to the olefinic substrate, the method being of a type which employs a reaction solution which includes osmium as a catalyst, a chiral ligand for enantiomerically directing said asymmetric addition, the olefinic substrate being present and soluble at a stoichiometric concentration within the reaction solution, the osmium bing present and soluble within the reaction solution at a catalytic concentration,

• wherein the improvement comprises the following substeps:
• Substep A:
• said asymmetric addition is performed using a sulfonamide as the nitrogen source for forming an asymmetric hydroxysulfonamide intermediate;
• and then:
• Substep B:
• said conversion is completed by deprotecting the asymmetric hydroxysulfonamide intermediate in said Substep A for forming the asymmetric hydroxylamine product.