Asymmetric dihydroxylation of vinyl sulfones: routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones |
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Authors: | Paul Evans Mélanie Leffray |
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Institution: | Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK |
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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 maritolide, are described. |
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Keywords: | asymmetric dihydroxylation vinyl sulfones prochiral alkene α-hydroxyaldehydes |
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