Synthesis of Diverse γ-Aryl-β-ketoesters via Aryne Intermediates Generated by C–C Bond Cleavage
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- Keisuke Uchida
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
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- Yasunori Minami
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
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- Suguru Yoshida
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
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- Takamitsu Hosoya
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
書誌事項
- 公開日
- 2019-10-24
- 資源種別
- journal article
- 権利情報
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- https://doi.org/10.15223/policy-029
- https://doi.org/10.15223/policy-037
- https://doi.org/10.15223/policy-045
- DOI
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- 10.1021/acs.orglett.9b03418
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
A synthetic method for diverse γ-aryl-β-ketoesters through γ-aryl-β-ketoester-type arynes triggered by C-C bond cleavage has been developed. The Mukaiyama aldol reaction of 6-(triflyloxy)benzocyclobutenones with ketene silyl acetals and subsequent treatment of resulting 6-(triflyloxy)benzocyclobutenols with a base triggered the efficient generation of γ-aryl-β-ketoester-type arynes, which reacted with various arynophiles to provide a wide range of γ-aryl-β-ketoesters. The synthetic utility of the method was demonstrated by the synthesis of an analog of ALK inhibitor.
収録刊行物
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- Organic Letters
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Organic Letters 21 (22), 9019-9023, 2019-10-24
American Chemical Society (ACS)