Synthesis of Chiral Cyclopropyl Carbocyclic Purine Nucleosides via Asymmetric Intramolecular Cyclopropanations Catalyzed by a Chiral Ruthenium(II) Complex

被引：32

作者：

Huang, Ke-Xin ^{[1
]}

Xie, Ming-Sheng ^{[1
]}

Zhao, Guo-Feng ^{[1
]}

Qu, Gui-Rong ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 22期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

asymmetric catalysis; carbocyclic nucleosides; cyclopropanation; enantioselectivity; NUCLEOBASE SUBSTITUTED ACRYLATES; LOWER METHYLENE HOMOLOG; ENANTIOSELECTIVE SYNTHESIS; ACYCLIC NUCLEOSIDES; ANTIVIRAL ACTIVITY; 3+2 CYCLOADDITION; ANALOGS; OLEFINS; POTENT; DIAZOACETATES;

D O I：

10.1002/adsc.201600377

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of chiral cyclopropyl carbocyclic purine nucleoside analogues via the highly enantioselective intramolecular cyclopropanation reactions has been reported. With a chiral ruthenium(II)-phenyloxazoline complex as the catalyst, cyclopropyl carbocyclic purine nucleoside analogues containing three contiguous stereocenters were obtained with up to 99% yield and 99% ee. Furthermore, a chiral cyclopropyl carbocyclic adenosine nucleoside having anti-BLV activity could be synthesized in a concise manner using this strategy.

引用

页码：3627 / 3632

页数：6

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