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DOI | 10.1038/ncomms16104 |
Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions | |
Xiong, Qian; Dong, Shunxi; Chen, Yushuang; Liu, Xiaohua; Feng, Xiaoming | |
2019-05-09 | |
发表期刊 | NATURE COMMUNICATIONS |
ISSN | 2041-1723 |
出版年 | 2019 |
卷号 | 10 |
文章类型 | Article |
语种 | 英语 |
国家 | Peoples R China |
英文摘要 | Although isocyanide-based multicomponent reactions were proven to be simple, elegant and facile strategies for the synthesis of highly valuable nitrogen-containing heterocycles, their asymmetric versions accessing to optically active nitrogen heterocyclic compounds are rather limited. Here, we illustrate that, relying on the enantioselective addition of simple isocyanides to C=C bonds, several isocyanide-based multicomponent reactions are realized in the presence of a chiral Mg-II-N,N'-dioxide catalyst. In the reaction among isocyanide, TMSN3, and alkylidene malonate, three- or four-component reactions could be precisely controlled by modulating reaction conditions, supplying two types of enantioenriched tetrazole-derivatives in moderate to high yields. Possible catalytic cycles via a key zwitterionic intermediate, and the vital roles of H2O or excess ligand are provided based on control experiments. Moreover, taking advantage of this zwitterionic intermediate as a 1,3-dipole, an enantioselective dearomative [3+2] annulation reaction of nonactivated isoquinolines is achieved, furnishing chiral 1,2-dihydroisoquinolines in good to excellent results. |
领域 | 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000467535100002 |
WOS关键词 | HETEROCYCLIC STRUCTURES ; CYCLOADDITION ; CHEMISTRY ; DEAROMATIZATION ; METHYLIDES ; ALKALOIDS ; INSERTION ; CATALYST ; LIGANDS ; BOND |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/203392 |
专题 | 资源环境科学 |
作者单位 | Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China |
推荐引用方式 GB/T 7714 | Xiong, Qian,Dong, Shunxi,Chen, Yushuang,et al. Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions[J]. NATURE COMMUNICATIONS,2019,10. |
APA | Xiong, Qian,Dong, Shunxi,Chen, Yushuang,Liu, Xiaohua,&Feng, Xiaoming.(2019).Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions.NATURE COMMUNICATIONS,10. |
MLA | Xiong, Qian,et al."Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions".NATURE COMMUNICATIONS 10(2019). |
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