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Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation.

Authors :
Xu X
Peng L
Chang X
Guo C
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2021 Dec 15; Vol. 143 (49), pp. 21048-21055. Date of Electronic Publication: 2021 Dec 03.
Publication Year :
2021

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.

Details

Language :
English
ISSN :
1520-5126
Volume :
143
Issue :
49
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
34860020
Full Text :
https://doi.org/10.1021/jacs.1c11044