Amidation of Aldehydes and Alcohols through α‐Iminonitriles and a Sequential Oxidative Three‐Component Strecker Reaction/Thio‐Michael Addition/Alumina‐Promoted Hydrolysis Process to Access β‐Mercaptoamides from Aldehydes,Amines, and Thiols |
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Authors: | Jean‐Baptiste Gualtierotti Xavier Schumacher Dr. Patrice Fontaine Dr. Géraldine Masson Dr. Qian Wang Prof. Dr. Jieping Zhu |
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Affiliation: | 1. Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL‐SB‐ISIC‐LSPN, BCH 5304, 1015 Lausanne (Switzerland), Fax: (+41)?21‐6939740;2. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif‐sur‐Yvette Cedex (France) |
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Abstract: | Mild and general alumina‐promoted hydrolysis conditions for converting α‐iminonitriles into carboxamides have been developed. In combination with the oxidative three‐component Strecker reaction, the one‐pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf)3‐catalyzed Michael addition of thiols to α,β‐unsaturated α‐iminonitriles is reported for the synthesis of β‐mercapto‐α‐iminonitriles. The successful integration of an oxidative Strecker reaction, thio‐Michael addition, and neutral‐alumina‐promoted hydrolysis of β‐mercapto‐α‐iminonitriles into a three‐component one‐pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β‐mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes. |
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Keywords: | alumina amides Michael addition multicomponent reactions Strecker reaction |
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