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

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

Published:2014-05-01 Issue:5 Volume:12 Page:586-593
ISSN:2391-5420
Container-title:Open Chemistry
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Author:

Jasiński Radomir¹,Ziółkowska Magda²,Demchuk Oleh³,Maziarka Agata¹

Affiliation:

1. 1Cracow University of Technology

2. 2AGH University of Science and Technology

3. 3Maria Curie-Sklodowska University

Abstract

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.

Publisher

Walter de Gruyter GmbH

Subject

Materials Chemistry,General Chemistry

Link

http://link.springer.com/content/pdf/10.2478/s11532-014-0518-2.pdf

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