Issue 3, 2014

Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis

Abstract

A class of conformationally flexible ligands composed of a tertiary amino oxide–amide backbone and a straight-chain alkyl spacer was developed. These C2-symmetric chiral N,N′-dioxide ligands could be straightforwardly synthesized from readily available amino acids and amines. They act as neutral tetradentate ligands to bind a wide variety of metal ions. Non-planar cis-α M(N,N′-dioxide) complexes enable an intriguing and easily fine-tuned chiral platform for a number of asymmetric reactions. Privileged N,N′-dioxide ligands frequently show wide substrate generality and exceptional levels of stereocontrol for a specific catalytic reaction. We describe approaches to the ligand design and synthesis, structure and bonding in coordination complexes, and the recent developments in asymmetric catalysis.

Graphical abstract: Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis

Supplementary files

Article information

Article type
Tutorial Account
Submitted
29 Nov 2013
Accepted
05 Jan 2014
First published
04 Feb 2014

Org. Chem. Front., 2014,1, 298-302

Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis

X. Liu, L. Lin and X. Feng, Org. Chem. Front., 2014, 1, 298 DOI: 10.1039/C3QO00059A

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