Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate

A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polys...

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Veröffentlicht in:European journal of organic chemistry 2019-09, Vol.2019 (34), p.5985-5991
Hauptverfasser: Hao, Feiyue, Gu, Zhenyu, Liu, Guyue, Yao, Wubing, Jiang, Huajiang, Wu, Jiashou
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Sprache:eng
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Zusammenfassung:A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polysubstituted acetamides and 2‐arylindole derivatives. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds. A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901073