75958-95-1Relevant academic research and scientific papers
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.
AN IMPROVED PROCEDURE FOR THE TWO CARBON HOMOLOGATION OF ESTERS TO α,β-UNSATURATED ESTERS
Takacs, James M.,Helle, Mark A.,Seely, Franklin L.
, p. 1257 - 1260 (2007/10/02)
Treatment of esters with diisobutylaluminium hydride (DIBAL) in the presence of lithio-trialkylphosphonoacetate results in improved yields of the homologated α,β-unsaturated esters.The problematic overreduction, which has previously observed in the half reduction of esters using DIBAL, is minimal (3percent) under these conditions.
