This research demonstrates reversed regioselectivity in the cycloaddition reaction of nitrones with enals, suggesting new pathways for synthetic applications.
The 1,3-dipolar cycloaddition of nitrones with hydrazones affords 5-iminoisoxazolidines as the major products, in contrast to the reaction with enals, which exclusively afford 4-acylisoxazolidines. This reversal of regioselectivity can be explained in terms of frontier orbital theory. The 5-iminoisoxazolidines are easily converted to 5-acylisoxazolidines.
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Maeda et al. (2026) studied this question.
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