Enantioselective Radical Addition of Alkyl Halides to Glyoxylate Oxime Ether

Significance

Quaternary ammonia salts of cinchona alkaloids quinine and quinidine and hypophosphorous acid have been employed to provide a chiral environment for the addition of an alkyl radical to glyoxylate oxime ether. The reaction was found to proceed with moderate to good yields and varying degrees of enantioselectivities. The highest enantioselectivity was observed for sterically demanding alkyl halides. The described method offers mild and practical reaction conditions: The glyoxylate oxime ether is generated in situ and the reaction is run at room temperature.