SULFAMOYLATION OF ESTER ENOLATE ANIONS |
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| Authors: | W Franklin Gilmore David W Morton |
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| Institution: | Department of Medicinal Chemistry , School of Pharmacy, University of Mississippi , University, MS, 38677 |
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| Abstract: | Abstract Stabilized carbanions such as the α-carbanions of carboxylic acid esters react with sulfamoyl chlorides by nucleophilic displacement at chlorine which results in chlorination of the carbanion. Thus direct sulfamoylation of these carbanions with sulfamoyl chlorides fails. Conversion of sulfamoyl chlorides to N-sulfonylamines followed by addition of carbanions at -78°C results in sulfamoylation of the carbanion. The method has not been successful with carbanions from diethyl acetamidomalonate and ethyl diphenylacetate. |
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| Keywords: | Sulfamoylation ester enolates sulfonylamines sulfamoylacetates carbalkoxylation sulfamoyl chlorides |
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