Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes
Date
2018-10-01Author
Garapati, Venkata Krishna Rao
Gravel, Michel
Publisher
ACS PublicationsType
ArticlePeer Reviewed Status
Peer ReviewedMetadata
Show full item recordAbstract
Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.