Carboxylate Anions Accelerate Pyrrolidinopyridine (PPy)-Catalyzed Acylation: Catalytic Site-Selective Acylation of a Carbohydrate by in Situ Counteranion Exchange
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- Masanori Yanagi
- Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan
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- Ayumi Imayoshi
- Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan
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- Yoshihiro Ueda
- Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan
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- Takumi Furuta
- Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan
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- Takeo Kawabata
- Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan
書誌事項
- 公開日
- 2017-05-30
- 資源種別
- journal article
- DOI
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- 10.1021/acs.orglett.7b01213
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
Acylpyridinium ions have been known as catalytically active species in acylation reactions catalyzed by 4-dimethylaminopyridine and its analogues. Acylpyridinium carboxylates were found to be 800-1300 times more reactive than the corresponding acylpyridinium chlorides. A catalytic cycle was developed, in which acylpyridinium carboxylates were generated by in situ counteranion exchange from the acylpyridinium chlorides. A catalyst loading as low as 0.01 mol % and catalyst turnover number of up to 6700 were achieved for site-selective acylation of a carbohydrate.
収録刊行物
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- Organic Letters
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Organic Letters 19 (12), 3099-3102, 2017-05-30
American Chemical Society (ACS)
