Tetrahedron

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

P Evans, M Leffray

Index: Evans, Paul; Leffray, Melanie Tetrahedron, 2003 , vol. 59, # 40 p. 7973 - 7981

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Citation Number: 55

Abstract

The asymmetric dihydroxylation of α, β-unsaturated sulfones under Sharpless conditions affords enantioenriched α-hydroxyaldehydes in a complex mixture of dimeric species. These mixtures undergo olefination generating the corresponding α, β-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 ...