Esterification of Maleamic Acids without Double Bond Isomerization

A Sánchez, E Pedroso…

Index: Sanchez, Albert; Pedroso, Enrique; Grandas, Anna European Journal of Organic Chemistry, 2010 , # 13 p. 2600 - 2606

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Abstract

Abstract Activation of the carboxylic acid group of a maleamic acid by treatment with an arenesulfonyl chloride followed by addition of an alcohol affords a fumaramate or a maleamate, depending on the reaction conditions. The E isomer is obtained when the acid is treated with nearly equimolar amounts of 2, 4, 6-triisopropylbenzenesulfonyl chloride and an alcohol in pyridine. Replacement of pyridine by 2-picoline and use of a larger excess of ...