Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts.
[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.
Peltier
Hillary M
HM
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
Evans
Jared W
JW
Ellman
Jonathan A
JA
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*
D002930:Cinchona Alkaloids; D004952:Esters; D007202:Indicators and Reagents; D013452:Sulfonium Compounds; D011802:Quinidine