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 activating agent (mesitylene-sulfonyl chloride) and alcohol affords the Z isomer. In both cases, high diastereomeric excesses and yields are achieved.
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