13038-15-8Relevant academic research and scientific papers
In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols
Phillips, David J.,Graham, Andrew E.
, p. 649 - 652 (2008/12/20)
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.
Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters
Phillips, David J.,Pillinger, Kathryn S.,Li, Wei,Taylor, Angela E.,Graham, Andrew E.
, p. 10528 - 10533 (2008/02/13)
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.
