158504-57-5Relevant academic research and scientific papers
Synthesis of acetylenedicarboxylic acid esters and asymmetric Diels-Alder reactions of the bis(methyl (S)-lactyl) ester
Charlton, James L.,Chee, Gaiklean,McColeman, Heather
, p. 1454 - 1462 (2007/10/03)
A general method has been developed for the preparation of acetylenedicarboxylic acid esters and applied to the synthesis of both achiral and chiral esters.Diels-Alder reactions of one of the chiral esters, the bis(methyl (S)-lactyl) ester, with various types of dienes, such as phenylbutadiene, orthoquinodimethanes, and isobenzofuran, have been investigated.Moderate asymmetric induction was observed in reactions with dienes bearing an α-hydroxyl group.In one case, an unusual solvent-induced reversal of asymmetric induction was observed.Key words: acetylenedicarboxylic acid esters, phenylbutadiene, orthoquinodimethanes, isobenzofurans, Diels-Alder , asymmetric.
Synthesis of Chiral Esters of Acetylenedicarboxylic Acid
Charlton, James L.,Chee, Gaiklean
, p. 6243 - 6246 (2007/10/02)
A general method for the preparation of acetylenedicarboxylic acid esters has been investigated and several esters have been prepared in excellent yield.The bis-(methyl (S)-lactyl), bis-(methyl (R)-mandelyl), and bis-menthyl esters were prepared, as well as achiral diaryl and dialkyl esters.The esters were synthesized from the corresponding dibromofumarates by 2,3-dibromo elimination using zinc or zinc amalgam in THF at room temperature or at reflux.The dibromofumarates were prepared by the esterification of dibromofumaryl chloride with the corresponding alcohols.
