Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones

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.