Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 46, Pages 14812-14819Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202291
Keywords
alumina; amides; Michael addition; multicomponent reactions; Strecker reaction
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Funding
- EPFL
- Swiss National Centre of Competence in Research (NCCR)
- Swiss National Science Foundation (SNSF)
- ICSN
- CNRS (France)
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Mild and general alumina-promoted hydrolysis conditions for converting alpha-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 alpha,beta-unsaturated a-iminonitriles is reported for the synthesis of beta-mercapto-alpha-iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of beta-mercapto-alpha-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into beta-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes.
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