title: Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts.
abstract: [reaction: see text] Practical reaction conditions for the catalytic enantioselective synthesis of sulfinate esters are reported. Commercially available cinchona alkaloids were found to be superior catalysts for the sulfinyl transfer reaction of tert-butanesulfinyl chloride and a variety of benzyl alcohols. Sulfinyl transfer with 2,4,6-trichlorobenzyl alcohol and 10 mol % of the commercially available, inexpensive catalyst quinidine provided the pure sulfinate ester product in 92% isolated yield and with 90% ee.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Hillary M
authors.initials: HM
authors.lastname: Peltier
authors.forename: Jared W
authors.initials: JW
authors.lastname: Evans
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis; D007202:Indicators and Reagents; D015394:Molecular Structure; D011802:Quinidine / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000032:analysis / Q000138:chemical synthesis*
chemical_list: D002930:Cinchona Alkaloids; D004952:Esters; D007202:Indicators and Reagents; D013452:Sulfonium Compounds; D011802:Quinidine