Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

Abstract tert -Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert -butyl disulfide. Direct condensation of tert -butanesulfinamide with aldehydes and ketones provides tert -butanesulfinyl imines in uniformly high yields. The tert -butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.