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

Heterocyclic communications

article

A Guesmi¹  N Ben Hamadi² 

[1] Chemistry Department, College of Science, IMSIU (Al Imam Mohammad Ibn Saud Islamic University);Laboratory of Synthesis Heterocyclic and Natural Substances, Faculty of Sciences of Monastir, UM (University of Monastir);Textile Engineering Laboratory, Higher Institute of Technological Studies of Ksar Hellal, UM (University of Monastir)

关键词: Cycloaddition 1;    3-dipolar;    1;    5-dihydropyrrol-2-one;    arylnitrile oxides;    regiospecifically;    diastereoisomers;   

DOI  :  10.1515/hc-2019-0014

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

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.

【 授权许可】

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