Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts

Org Lett. 2005 Apr 28;7(9):1733-6. doi: 10.1021/ol050275p.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Esters / chemical synthesis
  • Indicators and Reagents
  • Molecular Structure
  • Quinidine / chemistry
  • Stereoisomerism
  • Sulfonium Compounds / analysis
  • Sulfonium Compounds / chemical synthesis*

Substances

  • Cinchona Alkaloids
  • Esters
  • Indicators and Reagents
  • Sulfonium Compounds
  • Quinidine