Selective synthesis of multifunctionalized cyclopent-3-ene-1-carboxamides and 2-oxabicyclo[2.2.1]heptane derivatives

被引：0

作者：

Zheng, Hui ^{[1
]}

Han, Ying ^{[1
]}

Xu, Feng-Shun ^{[1
]}

Sun, Jing ^{[1
]}

Yan, Chao-Guo ^{[1
]}

机构：

[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 36期

基金：

中国国家自然科学基金;

关键词：

STEREOCONTROLLED TRANSFORMATION; CONVENIENT SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; AMINO-ACIDS; NITROHEXOFURANOSES; CYCLOPENTYLAMINES; CONSTRUCTION; EFFICIENT; 4-OXOALKANE-1,1,2,2-TETRACARBONITRILES; MALONONITRILE;

D O I：

10.1039/d2nj03198a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Triethylamine promoted cycloaddition reaction of phenacylmalononitriles and o-hydroxychalcones in ethanol at room temperature gave multifunctionalized cyclopent-3-ene-1-carboxamides in good yields and with high diastereoselectivity. More importantly, the similar reaction of phenacylmalononitriles and chalcone o-enolates in ethanol at room temperature afforded functionalized 2-oxabicyclo[2.2.1]heptane derivatives in satisfactory yields and with high diastereoselectivity. A rational domino reaction was tentatively proposed to explain the selective formation of different cyclic compounds and the diastereoselectivity of the reaction.

引用

页码：17161 / 17166

页数：6

共 63 条

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