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

Takeda Norihiko | Zendy; Futaki Erika | Zendy; Kobori Yukiko | Zendy; Ueda Masafumi | Zendy; Miyata Okiko | Zendy

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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.

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