Theoretical study of the regioselectivity of the Huisgen reaction
Chen, Gang1,2; Yang, Jing1; Gao, Suo1; Zhang, Yu1; Hao, Xiao-jiang1
Corresponding AuthorYang, 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
Source PublicationRESEARCH ON CHEMICAL INTERMEDIATES
ISSN0922-6168
Volume39Issue:3Pages:1245-1250
AbstractFrom 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.
KeywordHuisgen Reaction Regioselectivity Regioisomer Pi-pi Stacking Theoretical Study
Subject AreaChemistry
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000316008300035
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/16419
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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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