Catalytic asymmetric aminohydroxylation of olefins with sulfonamides

摘要

beta -Hydroxyamines and beta -hydroxysulfonamides are synthesized from olefin substrates by means on a catalyzed asymmetric addition reaction. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhance regio- and enantio-selectivity. Sulfonamides are employed as an oxidant nitrogen source for the production of beta -hydroxysulfonamides. Excellent yields and enantiomeric efficiencies are achieved with co-solvents containing a 50/50 (v/v) mixtures of water and organic solvent. beta -Hydroxyamines are obtained by deprotecting the corresponding beta -hydroxysulfonamides.