Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3+2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines

被引：29

作者：

Zhang, Dan-Jie ^{[1
]}

Xie, Ming-Sheng ^{[1
]}

Qu, Gui-Rong ^{[1
]}

Gao, Yao-Wei ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Key Lab Green Chem Media & React,Minist Educ, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; NUCLEOBASE SUBSTITUTED ACRYLATES; AZOMETHINE YLIDES; PROLINE DERIVATIVES; CONSTRUCTION; CHEMISTRY; ACCESS; ACIDS; PYRROLIDINES; SILYLIMINES;

D O I：

10.1021/acs.orglett.6b00108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were Obtained in 86-99% yields, >20:1 dr, and 94 -> 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when alpha-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results.

引用

页码：820 / 823

页数：4

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