Phosphoric Acid Catalyzed Asymmetric 1,6‐Conjugate Addition of Thioacetic Acid to<i>para</i>‐Quinone Methides

DOI Web Site Web Site 被引用文献3件
  • Nan Dong
    State key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Department of Chemistry (Tianjin) Nankai University Tianjin 300071 China
  • Zhi‐Pei Zhang
    State key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Department of Chemistry (Tianjin) Nankai University Tianjin 300071 China
  • Xiao‐Song Xue
    State key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Department of Chemistry (Tianjin) Nankai University Tianjin 300071 China
  • Xin Li
    State key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Department of Chemistry (Tianjin) Nankai University Tianjin 300071 China
  • Jin‐Pei Cheng
    State key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Department of Chemistry (Tianjin) Nankai University Tianjin 300071 China

書誌事項

公開日
2015-12-08
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201509110
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>An asymmetric 1,6‐conjugate addition of thioacetic acid with<jats:italic>para</jats:italic>‐quinone methides has been developed by using chiral phosphoric acid catalysis in the presence of water. A series of sulfur‐containing compounds were thus obtained in high yields with good to excellent enantioselectivities. Theoretical studies indicated that the water‐bridged proton transfer is a potentially favorable reaction pathway. An unprecedented O−H⋅⋅⋅π interaction between water and the aromatic nucleus of chiral phosphoric acid was discovered to contribute significantly to the stereocontrol in the catalysis.</jats:p>

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