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- Title
Nucleophilic Arylation of N, O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process.
- Authors
Takeda, Norihiko; Futaki, Erika; Kobori, Yukiko; Ueda, Masafumi; Miyata, Okiko
- Abstract
A novel approach for the umpolung α-arylation of amides is presented. By the nucleophilic phenylation of O-silyl N,O-ketene acetals, generated in situ from N-alkoxy amides, a phenyl group can be introduced onto the α-carbon atom of amides through N−O bond cleavage in a two-step, one-pot process. The asymmetric synthesis of α-aryl amides through the diastereoselective arylation of a chiral N,O-ketene acetal is also described.
- Subjects
UMPOLUNG; ARYLATION; ACETAL resins; AMIDES; ASYMMETRIC synthesis; PHENYL group
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 51, p16560
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708665