Issue 32, 2022

ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles

Abstract

Bifunctional chiral 4-aryl-pyridine-N-oxides (ArPNO) were reported for the acylative kinetic resolution of 3-hydroxy-3-substituted oxindoles, where the oxygen acts as the nucleophilic site. Using less sterically hindered acetic anhydride, both the recovered tertiary heterocyclic alcohols and the ester products exhibited good to excellent results with s-factors up to 167. Control experiments supported the dual activation manner, where the N-oxide group and N–H proton in ArPNO were crucial for high selectivity and enhanced catalytic reactivity. Compared with the extensively used chiral NHC, isochalcogenourea, and DMAP catalysts, we found that chiral ArPNO were also efficient organocatalysts in the kinetic resolution of tertiary alcohols.

Graphical abstract: ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles

Supplementary files

Article information

Article type
Paper
Submitted
06 Jul 2022
Accepted
21 Jul 2022
First published
22 Jul 2022

Org. Biomol. Chem., 2022,20, 6351-6355

ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles

M. Yang, Y. Gao, M. Xie and H. Guo, Org. Biomol. Chem., 2022, 20, 6351 DOI: 10.1039/D2OB01205G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements