Asymmetric dihydroxylation of vinyl sulfones:: routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones

The asymmetric dihydroxylation of alpha,beta-unsaturated sulfones under Sharpless conditions affords enantioenriched alpha-hydroxyaldehydes in a complex mixture of dimeric species. These mixtures undergo olefination generating the corresponding alpha,beta-unsaturated esters or furan-2(5H)-ones with high levels of enantiomeric excess. The application of this method for the rapid stereoselective synthesis of the furanone natural products; quercus lactone and maritolide, are described. (C) 2003 Elsevier Ltd. All rights reserved.