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タイトル: | Direct Addition of Amides to Glycals Enabled by Solvation-Insusceptible 2-Haloazolium Salt Catalysis |
著者: | Nakatsuji, Yuya Kobayashi, Yusuke Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed) |
著者名の別形: | 中辻, 雄哉 小林, 祐輔 竹本, 佳司 |
キーワード: | Brønsted acid catalysis carbohydrates glycosylation organocatalysis |
発行日: | 1-Oct-2019 |
出版者: | Wiley |
誌名: | Angewandte Chemie |
巻: | 58 |
号: | 40 |
開始ページ: | 14115 |
終了ページ: | 14119 |
抄録: | The direct 2‐deoxyglycosylation of nucleophiles with glycals leads to biologically and pharmacologically important 2‐deoxysugar compounds. Although the direct addition of hydroxyl and sulfonamide groups have been well developed, the direct 2‐deoxyglycosylation of amide groups has not been reported to date. Herein, we show the first direct 2‐deoxyglycosylation of amide groups using a newly designed Brønsted acid catalyst under mild conditions. Through mechanistic investigations, we discovered that the amide group can inhibit acid catalysts, and the inhibition has made the 2‐deoxyglycosylation reaction difficult. Diffusion‐ordered two‐dimensional NMR spectroscopy analysis implied that the 2‐chloroazolium salt catalyst was less likely to form aggregates with amides in comparison to other acid catalysts. The chlorine atom and the extended π‐scaffold of the catalyst played a crucial role for this phenomenon. This relative insusceptibility to inhibition by amides is more responsible for the catalytic activity than the strength of the acidity. |
著作権等: | This is the peer reviewed version of the following article: [Angewandte Chemie, 58(40), 14115-14119], which has been published in final form at https://doi.org/10.1002/anie.201907129. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. The full-text file will be made open to the public on 26 September 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving' この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/244790 |
DOI(出版社版): | 10.1002/anie.201907129 |
PubMed ID: | 31392793 |
出現コレクション: | 学術雑誌掲載論文等 |
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