Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters |
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Authors: | David J Phillips |
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Institution: | Department of Chemistry, University of Wales Swansea, Swansea SA2 8PP, UK |
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Abstract: | The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC. |
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Keywords: | α β-Unsaturated hydroxy esters Tandem oxidation/olefination Manganese dioxide Diol desymmetrization |
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