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Pure Appl. Chem., 2003, Vol. 75, No. 1, pp. 39-46

Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

J. A. Ellman

Center for New Directions in Organic Synthesis, Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720, USA

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.