1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes

被引：21

作者：

Yao, Yongqi ^{[1
]}

Yang, Wen ^{[1
]}

Lin, Qifu ^{[1
]}

Yang, Weitao ^{[1
]}

Li, Huanyong ^{[2
]}

Wang, Lin ^{[2
]}

Gu, Fenglong ^{[1
]}

Yang, Dingqiao ^{[1
]}

机构：

[1] South China Normal Univ, Minist Educ, Sch Chem, Key Lab Theoret Chem Environm, Guangzhou 510006, Guangdong, Peoples R China

[2] Jinan Univ, Analyt & Testing Ctr, Guangzhou 510632, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 19期

基金：

中国国家自然科学基金;

关键词：

CATALYZED ASYMMETRIC ADDITION; RING-OPENING REACTIONS; OXABICYCLIC ALKENES; AZABICYCLIC ALKENES; AZOMETHINE YLIDES; RADICAL-ADDITION; ACCESS; WATER;

D O I：

10.1039/c9qo00660e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 1,3-dipolar cycloaddition of oxa(aza)bicyclic alkenes with nitrones has been developed. The operationally simple cycloaddition allows efficient synthesis of fused bicyclic tetrahydroisoxazoles bearing exo- and anti-five member heterocyclic rings (76-99% yields) without any catalyst and additive under mild conditions. The proposed concerted mechanism and the observed selectivity are investigated by DFT calculations of the reaction pathways. This mild and practical [3 + 2] cycloaddition provides an efficient route to access highly functionalized compounds.

引用

页码：3360 / 3364

页数：5

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