Cobalt(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective Synthesis of Benzothiadiazine‐1‐oxides via C−H Activation

  • Yuki Hirata
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan
  • Daichi Sekine
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan
  • Yoshimi Kato
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan
  • Luqing Lin
    Zhang Dayu School of Chemistry Dalian University of Technology Dalian 116024 P. R. China
  • Masahiro Kojima
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan
  • Tatsuhiko Yoshino
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan
  • Shigeki Matsunaga
    Faculty of Pharmaceutical Sciences Hokkaido University Kita-ku, Sapporo 060-0812 Japan

書誌事項

公開日
2022-05-19
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.202205341
  • 10.1002/ange.202205341
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Among sulfoximine derivatives containing a chiral sulfur center, benzothiadiazine‐1‐oxides are important for applications in medicinal chemistry. Here, we report that the combination of an achiral cobalt(III) catalyst and a pseudo‐<jats:italic>C</jats:italic><jats:sub>2</jats:sub>‐symmetric H<jats:sub>8</jats:sub>‐binaphthyl chiral carboxylic acid enables the asymmetric synthesis of benzothiadiazine‐1‐oxides from sulfoximines and dioxazolones via enantioselective C−H bond cleavage. With the optimized protocol, benzothiadiazine‐1‐oxides with several functional groups can be accessed with high enantioselectivity.</jats:p>

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