Synthesis p. 173 - 175 (1994)
Update date:2022-08-02
Topics:
Kishikawa
Eida
Kohmoto
Yamamoto
Yamada
Two methods for the chemoselective alcoholysis of acylureas were developed to generate esters and amides, respectively. In alcoholysis using sodium methoxide in methanol, methoxide attacked the acyl carbonyl to give the corresponding methyl ester. While in alcoholysis using lithium benzyloxide in diethyl ether, benzyloxide attacked the urea carbonyl to give the amide. The chemoselectivity originates in the different chelating abilities of the metals and the polarity of the solvents.
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