Faculty Profile

Faculty Profile of Hamish Christie

Hamish Christie

Lecturer/Organic Laboratory Manager

Email: hamishc@email.arizona.edu
Building: Koffler 322
Phone: 520-626-8311

Education and Appointments

  • B.Sc. 1996, The University of Adelaide
  • M.Sc. 1998, The University of Adelaide
  • Ph.D. 2003, The University of California, Berkeley
  • Postdoctoral Fellow 2004-2006, The University of North Carolina at Chapel Hill

Research Interests

  • Organic
  • Synthesis/Synthetic Methods Development

Research Summary

Our research interests relate to complex molecule synthesis. We investigate synthetic organic chemistry, with the goal of improving existing methods and discovering new processes including enantioselective reactions.

Catalysts with Multiple Lewis Acidic Sites
Typical contemporary examples of enantioselective Lewis acid catalysis involve strong binding of a reactant to a single Lewis acidic catalyst site. Stereoselective reaction then depends on, poorly predictable, steric interactions to orient and organize the reactants. Many functional groups, including the carbonyl group, are capable of binding to more than one Lewis acidic atom simultaneously. We are studying catalyst frameworks that make use of multiple Lewis acidic atoms to organize and orient reactant molecules for enantioselective reactions.

Multi-Functional Catalysts Bearing Lewis Acidic and Nucleophilic Sites
We are developing catalysts that are able to interact with substrate molecules by making use of more than one strong binding interaction. Both nucleophilic and electrophilic binding sites are being exploited. With multiple binding interactions reactants will be better organized, leading to more effective stereoselective reactions.

Artificial Hydrolases
We are interested in the challenge of developing synthetic hydrolases. In the hands of the organic chemist, hydrolysis of the amide bond typically requires brutal conditions. A comparison with the protease enzymes provides an awesome example of the deficiency of current synthetic methods, because clearly this transformation can be carried out rapidly at physiological temperature at near neutral pH.

Possible applications for an artificial hydrolase might include: better processes for producing biodiesel and the destruction of chemical weapons. The majority of biological processes involve the hydrolysis/formation of amide, phosphate, ester and glycosidic bonds. Consequently, artificial hydrolases might be expected to lead to applications for biological and biochemical investigations.

Natural Product Synthesis
The pursuit of natural product total synthesis has long provided a source of stimulating and exciting challenges in organic chemistry. We will pursue the synthesis of compounds with challenging molecular architecture, particularly those that also hold promise as important medicinal compounds or as tools for biological research.

Selected Publications

  • "Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries." Crimmins, M. T.; Christie, H. S.; Chaudhary, K.; Long, A. J. Am. Chem. Soc. 2005, 127, 13810-13812.
  • "Total synthesis of (±)-halichlorine, (±)-pinnaic acid and (±)-tauropinnaic acid." Christie, H. S.; Heathcock, C. H. Proc. Nat. Acad. Sci.: Natural Product Synthesis Special Feature 2004, 10, 12079-12084.