[3+2] Cycloadditions of nitrones as three-atom components to alkenes yield isoxazolidine cycloadducts,
which on chemical transformations can be converted to bioactive compounds. The [3+2] cycloadditions
route thus provides conversion of simple natural products to more complex naturally occurring bioactive
nitrogen heterocycles, and close analogues. As α,β-unsaturated amides abundantly occur as natural
products, [3+2] cycloadditions of nitrones with simpler α,β-unsaturated amides were studied to get
information about reactivity profiles. The reactions of C-(4-chlorophenyl)-N-methyl nitrone as
three-atom component to cinnamic acid anilides were investigated. The 3,4-trans-4,5-trans-4-
carboxanilido-2-methyl-3,5-diaryl isoxazolidines were the major cycloadducts; the diastereoisomeric
3,4-cis-4,5-trans-4-carboxanilido-2-methyl-3,5-diaryl isoxazolidines and regioisomeric 3,4-trans-4,5-
trans-5-carboxanilido-2-methyl-3,4-diaryl isoxazolidines were obtained as minor cycloadducts. The
cycloadducts were characterized by NMR studies and XRD analysis.