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Asymmetric catalysis with a chiral-at-osmium complex

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Abstract

The first example of a chiral osmium catalyst is reported in which the overall chirality originates exclusively from a stereogenic metal center (metal-centered chirality) with all coordinating ligands being achiral. The non-C2-symmetric chiral-at-metal complex contains two cyclometalated 7-methyl-1,7-phenanthrolinium heterocycles which can be described as two chelating pyridylidene remote N-heterocyclic carbene (rNHC) ligands. The octahedral coordination sphere is completed with one CO and one acetonitrile ligand. A monodentate chiral oxazoline ligand is used as a chiral auxiliary ligand to obtain enantiomerically pure chiral-at-osmium complexes (>99 : 1 e.r.). Finally, it is demonstrated that the developed chiral-at-osmium complex is suitable for ring-closing enantioselective C(sp3)–H aminations, including the first example of catalytic enantioselective cyclizations of azidoformates to chiral 2-oxazolidinones.

Graphical abstract: Asymmetric catalysis with a chiral-at-osmium complex

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Article information


Submitted
07 May 2020
Accepted
08 Jun 2020
First published
15 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Asymmetric catalysis with a chiral-at-osmium complex

G. Wang, Z. Zhou, X. Shen, S. Ivlev and E. Meggers, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03280H

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