Nucleophilic Arylation of N,O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process

Angewandte Chemie
Norihiko TakedaOkiko Miyata

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.

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Citations

Aug 29, 2018·Chemical Society Reviews·Daniel KaiserNuno Maulide
Nov 20, 2018·Organic & Biomolecular Chemistry·Norihiko TakedaOkiko Miyata
Feb 8, 2020·Organic & Biomolecular Chemistry·Erika FutakiMasafumi Ueda
Jun 20, 2021·Angewandte Chemie·Sebastian HeindlNuno Maulide
Aug 22, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ravi KumarSeunghoon Shin
Dec 19, 2020·Organic Letters·Norihiko TakedaMasafumi Ueda

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