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

Ke‐Xin Huang, Ming‐Sheng Xie, Guo‐Feng Zhao, Gui‐Rong Qu, Hai‐Ming Guo

doi:10.1002/adsc.201600377

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

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Ke‐Xin Huang

Key Laboratory of Green Chemical Media and Reactions Ministry of Education Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China
Ming‐Sheng Xie

Key Laboratory of Green Chemical Media and Reactions Ministry of Education Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China
Guo‐Feng Zhao

Key Laboratory of Green Chemical Media and Reactions Ministry of Education Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China
Gui‐Rong Qu

Key Laboratory of Green Chemical Media and Reactions Ministry of Education Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China
Hai‐Ming Guo

Key Laboratory of Green Chemical Media and Reactions Ministry of Education Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China

書誌事項

公開日: 2016-11-15

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/adsc.201600377

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>The synthesis of chiral cyclopropyl carbocyclic purine nucleoside analogues <jats:italic>via</jats:italic> 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% <jats:italic>ee</jats:italic>. Furthermore, a chiral cyclopropyl carbocyclic adenosine nucleoside having anti‐BLV activity could be synthesized in a concise manner using this strategy.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/png" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/adsc201600377-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text> </jats:p>