| Theoretical study of the regioselectivity of the Huisgen reaction | |
Chen, Gang1,2; Yang, Jing1 ; Gao, Suo1; Zhang, Yu1; Hao, Xiao-jiang1
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| 通讯作者 | Yang, J (reprint author), Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China. ; haoxj@mail.kib.ac.cn |
| 2013-03-01 | |
| 发表期刊 | RESEARCH ON CHEMICAL INTERMEDIATES
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| ISSN | 0922-6168 |
| 卷号 | 39期号:3页码:1245-1250 |
| 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. |
| 关键词 | Huisgen Reaction Regioselectivity Regioisomer Pi-pi Stacking Theoretical Study |
| 学科领域 | Chemistry |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000316008300035 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/16419 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 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 |
| 推荐引用方式 GB/T 7714 | Chen, Gang,Yang, Jing,Gao, Suo,et al. Theoretical study of the regioselectivity of the Huisgen reaction[J]. RESEARCH ON CHEMICAL INTERMEDIATES,2013,39(3):1245-1250. |
| APA | Chen, Gang,Yang, Jing,Gao, Suo,Zhang, Yu,&Hao, Xiao-jiang.(2013).Theoretical study of the regioselectivity of the Huisgen reaction.RESEARCH ON CHEMICAL INTERMEDIATES,39(3),1245-1250. |
| MLA | Chen, Gang,et al."Theoretical study of the regioselectivity of the Huisgen reaction".RESEARCH ON CHEMICAL INTERMEDIATES 39.3(2013):1245-1250. |
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