37976-30-0Relevant 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.
Preparation and photolysis of diaryl esters of acetylenedicarboxylic acid
Alvaro,Garcia,Miranda,Primo
, p. 3437 - 3444 (2007/10/02)
Two diaryl acetylenedicarboxylates 1 a,b have been prepared in moderate yields by direct reaction of acetylenedicarboxylic acid with the corresponding phenols catalyzed by sulfuric or p-toluenesulfonic acids and also through acetylenedicarbonyl chloride. The accompanying by-products have been characterized. Attempted esterification using N,N'-dicyclohexylcarbodiimide as condensing agent gives an asymmetric ester amide 11a and a substituted uracil 12a. Photolysis of the aryl ester 1 a,b in benzene solution affords the benzocoumaran-3-ones 14 a,b. In the case of 1b, minor amounts of a polycyclic condensed 4-chromanone 17b have also been observed. These results show that the nature of the substituent attached at the β-position of the C ≡ C triple bond plays an important role in the cyclization of o-hydroxyaryl ethynyl ketones.
