Organic Letters 2005-04-28

Catalytic enantioselective sulfinyl transfer using cinchona alkaloid catalysts.

Hillary M Peltier, Jared W Evans, Jonathan A Ellman

Index: Org. Lett. 7(9) , 1733-6, (2005)

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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.