Abstract The regiospecific 1,3-dipolar cycloaddition of 1,5-dihydropyrrol-2-one and arylnitrile oxides derivatives have been investigated. The asymmetric induction expected by the chiral centre of the 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives was very effective, single diastereoisomers anti-3 was formed. The diastereoselectivity was linked to the destabilization of the syn transition state as a result of the electrostatic repulsion between the hydroxy group of the dihydropyrrol-2-one derivatives and the atom oxygen of the dipole.

中文翻译：

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对芳基腈氧化物与 pyrrol-2-one 衍生物环加成反应总立体选择性的显着电子效应

摘要 研究了 1,5-二氢吡咯-2-酮和芳基腈氧化物衍生物的区域专一性 1,3-偶极环加成反应。5-羟基-3-甲基-1,5-二氢吡咯-2-one衍生物的手性中心所预期的不对称诱导非常有效，形成了单一的非对映异构体anti-3。由于二氢吡咯-2-一衍生物的羟基与偶极子的原子氧之间的静电排斥，非对映选择性与顺式过渡态的不稳定有关。