Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride

Jared W Evans; Matthew B Fierman; Scott J Miller; Jonathan A Ellman

doi:10.1021/ja047845l

Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride

J Am Chem Soc. 2004 Jul 7;126(26):8134-5. doi: 10.1021/ja047845l.

Authors

Jared W Evans¹, Matthew B Fierman, Scott J Miller, Jonathan A Ellman

Affiliation

¹ Center for New Directions in Organic Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.

PMID: 15225052
DOI: 10.1021/ja047845l

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.