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Title: Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes
Authors: Demchuk, Oleg M.
Jasiński, Radomir
Ziółkowska, Magda
Maziarka, Agata
Keywords: [2+3] cycloaddition; Nitrone; Nitroalkene; Regioselectivity; Stereoselectivity
Issue Date: 2014
Publisher: Versita
Citation: "Central European Journal of Chemistry", 2014, Vol. 12, nr 5, s. 586-593
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.
DOI: 10.2478/s11532-014-0518-2
Appears in Collections:Artykuły naukowe (WNŚiNoZ)

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