Asymmetric catalysis with a chiral-at-osmium complex

Chemical Communications : Chem Comm
Guanghui WangEric Meggers

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.

References

Jan 1, 1993·Science·G A CrispinoK B Sharpless
Dec 20, 2002·Angewandte Chemie·Malin A AnderssonK Barry Sharpless
Feb 29, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Helgard G Raubenheimer, Stephanie Cronje
May 8, 2010·Chemical Communications : Chem Comm·Florence ColletPhilippe Dauban
Jun 5, 2013·Accounts of Chemical Research·Lei GongEric Meggers
Jul 5, 2013·Journal of the American Chemical Society·John Hartung, Robert H Grubbs
Apr 24, 2014·Journal of the American Chemical Society·Haohua HuoEric Meggers
Aug 20, 2014·Journal of the American Chemical Society·John HartungRobert H Grubbs
Mar 6, 2015·Journal of the American Chemical Society·Denis SpasyukDmitry G Gusev
Apr 9, 2015·Chemistry : a European Journal·James P C CoverdalePeter J Sadler
Oct 30, 2016·Chemistry, an Asian Journal·Guo-Qiang XuPeng-Fei Xu
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jan 28, 2017·Accounts of Chemical Research·Lilu Zhang, Eric Meggers
Mar 16, 2017·Journal of the American Chemical Society·Yu ZhengEric Meggers
Jun 27, 2017·Journal of the American Chemical Society·Huiling JiangX Peter Zhang
Aug 8, 2017·Chemistry, an Asian Journal·Lilu Zhang, Eric Meggers
Jan 6, 2018·Journal of the American Chemical Society·María CarmonaDaniel Carmona
Feb 1, 2015·Chemical Science·Chuanyong WangEric Meggers
Mar 7, 2019·Journal of the American Chemical Society·Yubiao HongEric Meggers
Mar 7, 2019·Accounts of Chemical Research·Xiaoqiang Huang, Eric Meggers
Oct 18, 2019·Journal of the American Chemical Society·Yang HuX Peter Zhang

❮ Previous
Next ❯

Citations

Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ricardo Cerón-CamachoRonan Le Lagadec
Apr 17, 2021·Chemistry : a European Journal·Yubiao HongEric Meggers

❮ Previous
Next ❯

Methods Mentioned

BETA
silica gel
X-ray
circular dichroism
NMR

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.