Theoretical study of the regioselectivity of the Huisgen reaction

被引：12
作者：
Chen, Gang [1 ,2 ]
Yang, Jing [1 ]
Gao, Suo [1 ]
Zhang, Yu [1 ]
Hao, Xiao-jiang [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
[2] Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710065, Shaanxi, Peoples R China
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2013年 / 39卷 / 03期
关键词：
Huisgen reaction; Regioselectivity; Regioisomer; pi-pi Stacking; Theoretical study; 1,3-DIPOLAR;
D O I：
10.1007/s11164-012-0680-0
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
From the structure of a series of spiro (pyrrolidine-2,3'-oxindole) derivatives synthesized by Huisgen reaction of isatin, alpha-amino acids, and different olefins, different regioselectivities were found. The possible mechanism of the Huisgen reaction of oxindole azomethine ylide and the substituent of olefins was investigated using a B3LYP/6-311G* level of theory, and the results show that the regioselection depends on the energy barrier between the stacking state and the regioisomer. This mechanism can also be applied to the illumination of other Huisgen reactions.
引用
收藏
页码：1245 / 1250
页数：6
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