Organic chemistry: Asymmetric synthesis of chiral vicinal diamines

Summary

The project involves the development of new catalytic, asymmetric methods towards chiral vicinal diamines, of importance in chemical industry and medicine.

Supervisor(s)

Dr Matthew Todd

Research Location

School of Chemistry

Program Type

Masters/PHD

Synopsis

Chiral vicinal diamines are of wide importance in industrial chemical synthesis, catalysis and medicine (1). This project aims to discover new routes to these privileged structures via atom-efficient catalytic, asymmetric methods. Through iterative catalyst evaluation, using both rational design and combinatorial discovery, we hope to demonstrate new types of organic ligands displaying high catalyst efficiency (low mol%, low molecular weight, high yields and enantiomeric excesses) that operate under ambient conditions.
     Development of these catalysts, and efficient route towards their synthesis, will allow us to generate a number of novel processes of interest to the process and pharmaceutical sector. We will also be able to use these methods in the enantioselective synthesis of praziquantel, a drug used worldwide in the treatment of the tropical disease schistosomiasis (2). Such a target is a genuine test of our ability to catalyse important organic reactions enantioselectively, since the drug needs to be produced as a single enantiomer for the extremely low price of 23 cents per gram! How do we achieve this synthetic capability? Answer: with the discovery and design of new synthetic organic chemistry.

  1. D. Lucet, T. Le Gall and C. Mioskowski, Angew. Chem. Int. 1998, 37, 2580-2627.
  2. See http://www.thesynapticleap.org/schist/projects for a description of our activities in this area.

Additional Information

Project costs (chemicals, consumables, spectroscopy) are covered through existing funding in the group. Australian candidates are expected to be covered by an Australian Postgraduate Award. There is no direct funding for fees/salary of potential international students, but assistance will be given to good candidates (ideally with a research publication) who apply for scholarships to study at the University.

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Keywords

Bilharzia, organic synthesis, Organic chemistry, asymmetric synthesis, catalysis, diamines, enantiomeric excess, chirality, schistosomiasis, open source, tropical disease, Medicinal chemistry, pharmaceuticals, industry.

Opportunity ID

The opportunity ID for this research opportunity is: 129

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