Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives

IF 1.5 3区化学 Q3 CHEMISTRY, ORGANIC

Heterocyclic Communications Pub Date : 2019-01-01 DOI:10.1515/hc-2019-0014

A. Guesmi, N. B. Hamadi

引用次数: 0

Abstract

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.

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对芳腈氧化物与吡咯-2- 1衍生物环加成反应的总立体选择性有显著的电子效应

摘要研究了1，5-二氢吡咯-2-酮和芳基氮氧化物衍生物的区域特异性1，3-偶极环加成反应。5-羟基-3-甲基-1,5-二氢吡咯-2-酮衍生物的手性中心所预期的不对称诱导是非常有效的，形成了单个非对映异构体抗-3。由于二氢吡咯-2-酮衍生物的羟基与偶极的原子氧之间的静电排斥，非对映选择性与同过渡态的不稳定有关。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heterocyclic Communications 化学-有机化学

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

1.4 months

期刊介绍： Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.