Tetrahedron

Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

DJ Phillips, KS Pillinger, W Li, AE Taylor, AE Graham

Index: Phillips, David J.; Pillinger, Kathryn S.; Li, Wei; Taylor, Angela E.; Graham, Andrew E. Tetrahedron, 2007 , vol. 63, # 42 p. 10528 - 10533

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Citation Number: 28

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 ...