One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones

WCC 4

Jessica Tanuwidjaja, Department of Chemistry, University of California, Berkeley, CA 94720, Hillary M. Peltier, hpeltier@berkeley.edu, Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720, and Jonathan A. Ellman, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720.
A one-pot method for the asymmetric synthesis of tert-butanesulfinyl-protected amines is described. Condensation of aryl alkyl and dialkyl ketones with tert-butanesulfinamide followed by in situ reduction with the appropriate reagent provides either diasteromer of the sulfinamide products in good yields and with diastereomeric ratios of up to 99:1.

 

Many Faces of Chemistry: The Merck Index Women in Chemistry Award Symposium
9:15 AM-11:50 AM, Monday, August 20, 2007 Westin Boston Waterfront -- Revere, Oral

Women Chemists Committee

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007