In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols
An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields. Georg Thieme Verlag Stuttgart.
Phillips, David J.,Graham, Andrew E.
p. 649 - 652
(2008/12/20)
Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters
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.
Phillips, David J.,Pillinger, Kathryn S.,Li, Wei,Taylor, Angela E.,Graham, Andrew E.
p. 10528 - 10533
(2008/02/13)
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