Collect. Czech. Chem. Commun. 2009, 74, 1341-1349
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


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.