Enecarboxylation with diethyl oxomalonate as an enophilic equivalent of carbon dioxide. A synthesis of allylcarboxylic acids

MF Salomon, SN Pardo…

Index: Salomon, Mary F.; Pardo, Simon N.; Salomon, Robert G. Journal of the American Chemical Society, 1984 , vol. 106, # 13 p. 3797 - 3802

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Citation Number: 24

Abstract

Abstract: Allylcarboxylic acids are prepared from alkenes by a two-stage process which is synthetically equivalent to an ene reaction of carbon dioxide:(1) ene reaction with diethyl oxomalonate to afford an a-hydroxylmalonic ester and (2) oxidative bisdecarboxylation of the derived a-hydroxymalonic acid. The oxidative bisdecarboxylation of a-hydroxymalonic acids can sometimes be achieved with sodium periodate. However, occasionally ...