A strategy for the synthesis of isoxazoline-N-oxides (cyclic five-membered nitronates) from primary nitro compounds and olefins is described. The key step of the process involves 1,3-dipolar cycloaddition of corresponding 1-bromosilyl nitronates with alkenes. [reaction: see text]

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Compounds. -Optimal methods are detailed for the synthesis of five-membered cyclic nitronates from aliphatic nitro compounds and olefins. Under certain reaction conditions intermediates of the transformation such as (XII), (XIII) and (XIV) can be isolated. -(KUNETSKY, R. A.; DILMAN*, A. D.; STRUCHKOVA, M. I.; BELYAKOV, P. A.; TARTAKOVSKY, V. A.; IOFFE, S. L.; Synthesis 2006, 13, 2265-2270; Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia; Eng.) -Mais 45-129