Construction of All‐Carbon Quaternary Stereocenters <i>via</i> Asymmetric Cyclopropanations: Synthesis of Chiral Carbocyclic Pyrimidine Nucleosides

Hai‐Xia Wang, Fang‐Juan Guan, Ming‐Sheng Xie, Gui‐Rong Qu, Hai‐Ming Guo

doi:10.1002/adsc.201800222

Construction of All‐Carbon Quaternary Stereocenters <i>via</i> Asymmetric Cyclopropanations: Synthesis of Chiral Carbocyclic Pyrimidine Nucleosides

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Hai‐Xia Wang

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University Xinxiang, Henan 453007 People's Republic of China
Fang‐Juan Guan

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

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

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

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

書誌事項

公開日: 2018-04-20

権利情報

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

DOI

10.1002/adsc.201800222

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>An efficient route to synthesize chiral carbocyclic pyrimidine nucleoside analogues containing all‐carbon quaternary stereocenters has been established <jats:italic>via</jats:italic> the asymmetric intermolecular cyclopropanation of N1‐vinylpyrimidines and α‐aryl diazoesters. With 2 mol% of chiral dirhodium (II) carboxylate complex as the catalyst, a variety of chiral carbocyclic cytosine or uracil nucleoside analogues were obtained in good yields (up to 96% yield), high diastereoselectivities (>20:1 dr), and excellent enantioselectivities (up to 99% <jats:italic>ee</jats:italic>).</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/adsc201800222-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text> </jats:p>