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      Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes

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      Date
      2018-10-01
      Author
      Garapati, Venkata Krishna Rao
      Gravel, Michel
      Publisher
      ACS Publications
      Type
      Article
      Peer Reviewed Status
      Peer Reviewed
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      Abstract
      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.
      Citation
      Garapati, V. K. R.; Gravel, M. Org. Lett. 2018, 20, 6372-6375. https://doi.org/10.1021/acs.orglett.8b02636
      URI
      http://hdl.handle.net/10388/13181
      DOI
      10.1021/acs.orglett.8b02636
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