Triazole‐Based Anion‐Binding Catalysis for the Enantioselective Dearomatization of <i>N</i>‐Heteroarenes with Phosphorus Nucleophiles
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- Theresa Fischer
- Institute for Organic Chemistry University of Regensburg Universitätsstr. 31 93053 Regensburg Germany
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- Qui‐Nhi Duong
- Institute for Organic Chemistry University of Regensburg Universitätsstr. 31 93053 Regensburg Germany
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- Olga García Mancheño
- Institute for Organic Chemistry University of Regensburg Universitätsstr. 31 93053 Regensburg Germany
書誌事項
- 公開日
- 2017-02-16
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/chem.201605660
- 公開者
- Wiley
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>The first enantioselective synthesis of chiral heterocyclic α‐amino phosphonates by nucleophilic dearomatization of quinolines and pyridines using an anion‐binding organocatalysis approach is described. Chiral tetrakistriazoles were employed as efficient hydrogen‐bond donor catalysts by forming a chiral close ion‐pair with the in situ formed <jats:italic>N</jats:italic>‐acyl salts and 2,2,2‐trichlorethoxycarbonyl chloride (TrocCl). The ion‐pair was subsequently treated with various phosphorus nucleophiles, such as silyl‐protected dialkyl‐ and trialkylphosphites. Thus, the corresponding products were obtained in complete or high regioselectivities and up to 97:3 e.r. for quinolines or up to 89:11 e.r. for the more challenging pyridine substrates. This method allows for rapid access to substituted chiral cyclic α‐amino phosphonates, which can be easily transformed into phosphonic acid derivatives.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 23 (25), 5983-5987, 2017-02-16
Wiley