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
收藏
页码：3360 / 3364
页数：5
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