Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation.
J Am Chem Soc
; 143(49): 21048-21055, 2021 12 15.
Article
em En
| MEDLINE
| ID: mdl-34860020
ABSTRACT
A highly enantioselective O-propargylation catalyzed by combining a phosphine-nickel complex and an axially chiral sodium dicarboxylate has been developed. The transformation features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, offering an efficient approach to an array of enantioenriched O-propargyl hydroxylamines. Mechanistic studies support the presumed role of the chiral carboxylate as a counterion for nickel catalysis enabling the discovery of highly stereoselective transformations. The power of this reaction is illustrated by its application in the asymmetric total synthesis of potent firefly luciferase inhibitors and (S)-dihydroyashabushiketol.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ácidos Dicarboxílicos
/
Alcinos
/
Complexos de Coordenação
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article