ASYMMETRIC TRANSFER HYDROGENATION USING TETHERED LIGANDS
Lead Research Organisation:
University of Warwick
Department Name: Chemistry
Abstract
Many molecules can exist in one of a pair of mirror-images, or 'enantiomers', rather like a pair of hands. Many of the molecules which make up biological organisms (microbes, plants, animals, us...) exist only in a single enantiomer form. These include amino acids (which are used to make peptides and enzymes in the body), carbohydrates, and the chain of DNA (which also has a spiral with a single handedness). Anything we consume interacts with the molecules which make up our bodies. Because the molecules in our bodies are 'one handedness' then each of a pair of enantiomers will interact differently. As a result, there are many cases of enantiomeric molecules where one enantiomer has beneficial properties whilst the other may have none at all, or even be harmful. As a result, any new pharmaceutical compounds, or indeed any new molecular entities with the potential to exist as enantiomers, must be preparable in single-enantiomer form. This is challenging for the synthetic chemist, but represents one of the most important objectives of contemporary synthetic chemistry.In previous work, we have developed catalysts for the conversion of readily-available starting materials (ketones) into predominantly one handedness of an enantiomeric product (alcohols). In some cases the selectivity is very high. However in other cases it is not. In this proposal, we propose several modifications to our catalysts which are predicted to make them more appropriate for the reduction of a much wider series of substrates, thus increasing their overall usefulness. In the long term our objective is to develop ways of modifying our catalysts so that they can be employed for the selective synthesis of pure enantiomers of any desired target. This project represents an important step towards this objective.
Organisations
People |
ORCID iD |
Martin Wills (Principal Investigator) |
Publications
G Nedden H
(2016)
The Development of Phosphine-Free "Tethered" Ruthenium(II) Catalysts for the Asymmetric Reduction of Ketones and Imines.
in Chemical record (New York, N.Y.)
Gosiewska S
(2010)
Synthesis and use of a stable aminal derived from TsDPEN in asymmetric organocatalysis
in Tetrahedron Letters
Majewski A
(2010)
A Continuous-Flow Method for the Generation of Hydrogen from Formic Acid
in ChemSusChem
Martins J
(2009)
Ir(III) complexes of diamine ligands for asymmetric ketone hydrogenation
in Tetrahedron
Martins J
(2008)
Further 'tethered' Ru(II) catalysts for asymmetric transfer hydrogenation (ATH) of ketones; the use of a benzylic linker and a cyclohexyldiamine ligand
in Journal of Organometallic Chemistry
Martins J
(2009)
Asymmetric hydrogenation of ketones using Ir(III) complexes of N-alkyl-N'-tosyl-1,2-ethanediamine ligands
in Tetrahedron Letters
Morris D
(2010)
Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN)
in Tetrahedron Letters
Morris D
(2009)
Insights into Hydrogen Generation from Formic Acid Using Ruthenium Complexes
in Organometallics
Morris DJ
(2006)
The "reverse-tethered" ruthenium (II) catalyst for asymmetric transfer hydrogenation: further applications.
in The Journal of organic chemistry
N/a Martins
(2009)
Asymmetric hydrogenation of ketones using Ir(III) complexes of N-alkyl-N'-tosyl-1,2-ethanediamine ligands
in Tetrahedron Letters
Description | Asymmetric Imine Transfer Hydrogenation |
Amount | £22,000 (GBP) |
Funding ID | collaborative studentship |
Organisation | Dr. Reddy's Laboratories |
Sector | Private |
Country | India |
Start | 10/2007 |
End | 09/2011 |
Description | Asymmetric Imine Transfer Hydrogenation |
Amount | £22,000 (GBP) |
Funding ID | collaborative studentship |
Organisation | Dr. Reddy's Laboratories |
Sector | Private |
Country | India |
Start | 10/2007 |
End | 09/2011 |
Description | Asymmetric Organocatalysis |
Amount | £45,000 (GBP) |
Funding ID | WPRS award to Rina Soni |
Organisation | University of Warwick |
Sector | Academic/University |
Country | United Kingdom |
Start | 10/2008 |
End | 09/2011 |
Description | Asymmetric Transfer Hydrogenation of Imines. |
Amount | £301,135 (GBP) |
Funding ID | EP/F019424/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 01/2008 |
End | 03/2011 |
Description | Hydrogenation of ketones without transition metal catalysts. |
Amount | £134,230 (GBP) |
Funding ID | EP/G036993/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 09/2009 |
End | 02/2013 |
Description | MOLECULAR MODELLING FOR ORGANOMETALLIC COMPOUNDS: RU-ARENES AS CATALYSTS AND ANTI-CANCER DRUGS |
Amount | £309,786 (GBP) |
Funding ID | EP/F042159/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 01/2009 |
End | 04/2012 |
Description | SUPERGEN: Delivery of Sustainable Hydrogen |
Amount | £4,943,135 (GBP) |
Funding ID | EP/G01244X/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 10/2008 |
End | 03/2013 |
Description | Squeezing hydrogen out of biomass; new catalysts for clean energy generation |
Amount | £185,603 (GBP) |
Funding ID | EP/F061420/1 |
Organisation | Engineering and Physical Sciences Research Council (EPSRC) |
Sector | Public |
Country | United Kingdom |
Start | 10/2008 |
End | 09/2009 |
Title | Transhydrogenation catalyst |
Description | |
IP Reference | |
Protection | Patent granted |
Year Protection Granted | |
Licensed | No |