3 years ago

Nucleophilic Arylation of N,O-Ketene Acetals with Triarylaluminums: Access to alpha-Aryl Amides through an Umpolung Process

Erika Futaki, Yukiko Kobori, Masafumi Ueda, Norihiko Takeda, Okiko Miyata
A novel approach for the umpolung alpha-arylation of amides is presented. By means of nucleophilic phenylation of O-silyl N,O-ketene acetals, generated in situ from N-alkoxyamides, a phenyl group can be introduced onto the alpha-carbon of amides via N-O bond cleavage through a two-step, one-pot process. The asymmetric synthesis of alpha-aryl amides through the diastereoselective arylation of a chiral N,O-ketene acetal is also described.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708665

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