Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes

Demchuk, Oleg M.; Jasiński, Radomir; Ziółkowska, Magda; Maziarka, Agata

Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes

Files

Jasinski_Ziolkowska_Demchuk_Maziarka_Regio_and_stereoselectivity_of_polar_2+3_cycloaddition_reactions.pdf(570.36 KB)

Date

2014

Authors

Publisher

Versita

Abstract

[2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects.

Keywords

[2+3] cycloaddition, Nitrone, Nitroalkene, Regioselectivity, Stereoselectivity

Citation

"Central European Journal of Chemistry", 2014, Vol. 12, nr 5, s. 586-593