We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Organocatalytic α-Addition of Isocyanides to Aldehydes.
- Authors
Yamada, Takeshi; Hirose, Tomoyasu; Ōmura, Satoshi; Sunazuka, Toshiaki
- Abstract
α-Hydroxyamide is an important chemical component widely observed in biologically active natural products. One of the most direct methods to access a α-hydroxyamide is the Passerini-type reaction. However, this catalytic process was limited. Herein, we report the first examples of 3,5,6-trifluoro-2-pyridone-catalyzed α-addition of isocyanides to aldehydes, in the presence of water in benzene, to provide α-hydroxyamides. Various aldehydes and isocyanides performed well in this reaction to provide the α-hydroxyamides. Even highly constrained substrates were well tolerated. The reaction is not restricted by requirements of either inconvenient temperature control, inert atmosphere or dry solvent. The new catalytic reaction may open the way to development of asymmetric organocatalytic α-addition of isocyanides.
- Subjects
ISOCYANIDES; ALDEHYDES; ORGANOCATALYSIS; BENZENE; HYDROXY acids
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 2, p296
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403313