Collect. Czech. Chem. Commun.
2009, 74, 1341-1349
https://doi.org/10.1135/cccc2009037
Published online 2009-09-11 22:41:43
Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones
Radomir Jasiński
Institute of Organic Chemistry and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, Poland
Abstract
The cycloaddition reactions of nitroethene to (Z)-N-aryl-C-phenylnitrones lead to mixtures of stereoisomeric cis- and trans-2-aryl-4-nitro-3-phenylisoxazolidines. Regioselectivity of these reactions is determined by the character of nucleophile–electrophile interactions, while stereoselectivity is determined by the steric factors and the character of secondary orbital interactions.
Keywords: [2+3]Cycloadditions; Dipolar cycloadditions; Nitrones; Isoxazolidines; Nitroethene; Regioselectivity; Stereoselectivity; DFT calculations.
References: 25 live references.
