N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development

Lead Research Organisation: University of St Andrews
Department Name: Chemistry


Synthetic chemistry is used for the preparation of structurally complex materials on a molecular scale. Complexity in molecules is often associated with chirality - the fundamental property of a structure that renders it non-superimposable on its mirror image. For example, your right hand is chiral because it cannot be superimposed upon its mirror image (your left hand); the right hand is called the enantiomer of the left hand. Chirality also has important consequences, as it means that a right-handed glove cannot be worn on the left hand. This concept of chirality extends to the molecular level, where molecules can exist in two forms that differ only in that the arrangement of their atoms make them mirror images; indeed the majority of biochemical processes involve the interaction of chiral molecules that can exist in non-superimposable mirror image (enantiomeric) forms. This proposal investigates the application of a simple class of chiral organic molecule, known as N-heterocyclic carbenes, for their ability to catalyse selectively the formation of a single enantiomer of a given substance. A modular approach to the design and preparation of these reactive molecules that contain the necessary function and structure to promote catalysis will be used to succeed in this area. The effect of changing the structure of the N-heterocyclic carbene upon its reactivity will also be probed, and the application of these results to asymmetric synthesis and new chemical transformations investigated.


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Description This research grant allowed to probe, develop, and understand the reactivity of two classes of molecules, called N-heterocyclic carbenes and isothioureas, in making molecules of pharmaceutical interest.
Exploitation Route The reactivity showed by these molecules provided a platform for the development of new reaction methodologies that have been exploited in industrial collaborations and in research groups around the world.
Sectors Chemicals,Pharmaceuticals and Medical Biotechnology

Description Some of the catalysts developed and utilised in this research have been utilised by a commercial agrochemical company in order to make compounds of significant biological interest.
Sector Agriculture, Food and Drink,Chemicals,Pharmaceuticals and Medical Biotechnology
Impact Types Societal

Description Research partnership - Herbert Mayr (LMU Munich) 
Organisation Ludwig Maximilian University of Munich (LMU Munich)
Department University Clinic of Munich
Country Germany 
Sector Academic/University 
PI Contribution Research partnership that led to exchange of students and led to numerous joint publications
Collaborator Contribution Exchange of methodology and research placement for students to benefit knowledge exchange
Impact A number of joint publications serve as joint outputs from this collaboration
Start Year 2010