The lithiated intermediate derived from methyl 2-(benzylideneamino)propanoate and lithium bromide/triethylamine undergoes cycloaddition and Michael addition with methyl acrylate. 1,3-Dipole character of the intermediate is suggested on the basis of the product ratios obtained under a variety of conditions. The reaction mechanism via a four-centered transition state is proposed.
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Kanemasa et al. (1989) studied this question.
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