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Nucleophilic Arylation of N , O ‐Ketene Acetals with Triaryl Aluminum Reagents: Access to α‐Aryl Amides through an Umpolung Process
Author(s) -
Takeda Norihiko,
Futaki Erika,
Kobori Yukiko,
Ueda Masafumi,
Miyata Okiko
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201708665
Subject(s) - ketene , umpolung , chemistry , nucleophile , aryl , silylation , acetal , alkoxy group , reagent , medicinal chemistry , bond cleavage , nucleophilic addition , organic chemistry , combinatorial chemistry , catalysis , alkyl
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.