Journal
TETRAHEDRON
Volume 59, Issue 40, Pages 7973-7981Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.08.003
Keywords
asymmetric dihydroxylation; vinyl sulfones; prochiral alkene; alpha-hydroxyaldehydes
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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.
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