Issue 5, 2024

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Abstract

Expanding the chemical space of chiral N-oxides and chiral 2,2′-bipyridine ligands is in great demand in asymmetric catalysis. Herein, a new class of C2-symmetric bipyridine-tertiary amine-derived chiral N,N′-dioxide (bipyridine-2NO) ligands, featuring structural fine-tunability, chemical stability, and ready accessibility, was rationally designed and developed, and the effectiveness was demonstrated in a Ni(II)-catalyzed asymmetric Michael-type Friedel–Crafts alkylation reaction of indoles and β,γ-unsaturated α-keto esters. Excellent yields (up to 92%) and high enantioselectivities (up to 99% ee) were obtained for a wide range of substrates under mild conditions. These results demonstrated the promising potential of the chiral bipyridine-2NO scaffold as an efficient type of tetradentate ligand.

Graphical abstract: Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
21 Oct 2023
Accepted
06 Jan 2024
First published
15 Jan 2024

Org. Chem. Front., 2024,11, 1314-1321

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Y. Wang, P. Hu, X. Wang, K. Xu, Q. Wang, H. Wang and X. Liu, Org. Chem. Front., 2024, 11, 1314 DOI: 10.1039/D3QO01748F

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