NOVEL 3-COMPONENT COUPLING REACTION OF CARBODIIMIDE, METHYL HYDROGEN MALEATE, AND AN ALCOHOL OR AMINE - SYNTHESIS OF N-CARBAMOYLASPARTIC ACID-DERIVATIVES
K. Kishikawa et al., NOVEL 3-COMPONENT COUPLING REACTION OF CARBODIIMIDE, METHYL HYDROGEN MALEATE, AND AN ALCOHOL OR AMINE - SYNTHESIS OF N-CARBAMOYLASPARTIC ACID-DERIVATIVES, Journal of the Chemical Society. Perkin transactions. I, (9), 1994, pp. 1205-1209
A novel three-component coupling reaction of methyl hydrogen maleate 1
, a carbodiimide 2, and an alcohol or amine gave derivatives of N-carb
amoylaspartic acid (3) in moderate to excellent yields. in the couplin
g, an intramolecular Michael addition of the acylisourea 6 subsequentl
y occurs to give a new intermediate. 2-iminooxazolidin-5-one 7. The ad
dition of alcohol or amine to the second intermediate 7 completes the
three-component coupling.