Issue 24, 2023

Enantioselective construction of quaternary stereocenters via organocatalytic arylation of isoxazolin-5-ones with o-quinone diimides

Abstract

A bifunctional squaramide derived from Cinchona alkaloid catalyzes the enantioselective arylation of isoxazolin-5-ones with o-quinone diimides (o-QDIs) to give isoxazolin-5-ones featuring an arylated quaternary stereocenter in high yields and excellent enantioselectivities. To the best of our knowledge, this is the first reported enantioselective arylation of isoxazol-5-ones and the first application of o-QDIs as arylating reagents in asymmetric catalysis.

Graphical abstract: Enantioselective construction of quaternary stereocenters via organocatalytic arylation of isoxazolin-5-ones with o-quinone diimides

Supplementary files

Article information

Article type
Research Article
Submitted
28 sep 2023
Accepted
23 okt 2023
First published
24 okt 2023
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2023,10, 6081-6086

Enantioselective construction of quaternary stereocenters via organocatalytic arylation of isoxazolin-5-ones with o-quinone diimides

R. Torán, E. Portillo, A. Sanz-Marco, C. Vila and G. Blay, Org. Chem. Front., 2023, 10, 6081 DOI: 10.1039/D3QO01600E

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