Abstract
The reaction of isatin, ninhydrin and acenaphthenequinone with primary and secondary amines gives rise to stereospecific formation of intermediate azomethine ylides which can be trapped by cycloaddition to methyl acrylate or N-methylmaleimide. The regiochemistry of the cycloadditions to methyl acrylate is controlled by both frontier orbital and steric interactions with the latter dominating in the examples studied.
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