title: Improved synthesis of tert-butanesulfinamide suitable for large-scale production.
abstract: [reaction: see text] An improved synthesis of tert-butanesulfinamide that overcomes the scalability problems of the previous syntheses is described. The key step is the catalytic asymmetric oxidation of the inexpensive di-tert-butyl disulfide starting material. The new homogeneous reaction conditions utilize an inexpensive chiral ligand prepared in a single step from commercially available cis-1-amino-indan-2-ol. The reaction is performed at a 2.3 M concentration in the practical solvent acetone and can readily be run on a kilogram scale.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman