title: Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride.
abstract: Development of a new synthetic route to obtain enantiomerically enriched tert-butanesulfinate esters in excellent yields through catalytic enantioselective sulfinyl transfer is described. As little as 0.5 mol % of chiral amine catalysts was used to couple racemic tert-butanesulfinyl chloride with arylmethyl alcohols to provide sulfinate esters in near quantitative yields and with enantiomeric excesses up to 81%. The method represents the first example of the catalytic dynamic resolution of sulfinyl derivatives.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.
authors.forename: Jared W
authors.initials: JW
authors.lastname: Evans
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Fierman
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman