Journal
ARKIVOC
Volume -, Issue -, Pages 189-199Publisher
ARKAT USA INC
DOI: 10.3998/ark.5550190.0006.919
Keywords
azomethine ylides; imines; isocyanates; imidazolidines; cycloadditions
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Substituted imidazolidines ( and not imidazolidin-4-ones) are the unexpected cycloadducts obtained in the reaction between imines and isocyanates. The reaction is shown to take place via stepwise [ 3+2] cycloaddition between the N-metallated azomethine ylide formed in situ and the starting imine, followed by nucleophilic addition of the resulting imidazolidine on the sphybridized carbon atom of the isocyanate. Density-Functional Theory calculations provide a model for the mechanism of this unusual reaction and for the origins of the observed regio- and stereoselectivity.
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