Adam McCarter

Chemistry, Strathclyde

Tenure since 2014

Carbocyclisations based on difluorinated enols

The goal of the project is to develop a new reaction which can be used to build important target molecules directly and conveniently.Adammcarter

The target molecules are selectively fluorinated; nature makes very few fluorinated molecules and selective fluorination (the placement of one or more fluorine atoms at a key site in a molecule) has emerged as a powerful tool in the hands of a wide range of molecular scientists from enzymologists to drug designers. Selectively fluorinated molecules can be made by the replacement of hydrogen atoms with fluorinating agents.

A strategically different approach uses low-cost materials which already contain fluorine atoms and transforms them; this is known as building block methodology. This latter approach has been used to prepare fluorinated analogues of cyclitols and sugars from trifluoroethanol, an inexpensive and sustainable feedstock. Using the strong base/low temperature chemistry that has been developed within the Percy group Saegusa-Ito cyclisation precursors can be prepared in 2 synthetic steps. Adam's first year of research has involved studying aspects of the Saegusa-Ito cyclisation for the synthesis of difluorinated cyclohexenones. His current aim is to develop a new synthetic protocol which will provide similar fluorinated analogues in a concise and atom efficient process. 

Biography

Adam currently holds a first class degree MChem in Chemistry with Drug Discovery which he obtained from the University of Strathclyde being awarded the Sir George Beilby Memorial Medal Awarded to a meritorious final year student in each of the Departments of Pure and Applied Chemistry and Mechanical Engineering at the University Of Strathclyde.

Adam made the dean’s list and received a Faculty of Science Meritorious Award in both his first, second and third years. He was also awarded the Andersonian Centenary Prize from the University for his performance in the first year Chemistry class, the William Marr Prize (awarded to a student with a meritorious record in the 1st and 2nd Years of the degree course) and in 3rd year a prestigious Nuffield Scholarship.

Adam started his 4th year (July 2012) in an industrial position at the GlaxoSmithKline laboratories in Upper Merion, Philadelphia, US, working within the Heart Failure DPU. His work focussed on the synthesis of pharmaceutically active small molecules towards the design of a lead compound. For his placement year he was awarded a pass with Distinction.

Adam was granted a Carnegie Vacation Scholarship in 2011 which allowed him to undertake an 8-week summer placement within the University of Strathclyde Organic Laboratories investigating the scope of Suzuki−Miyaura couplings with potassium trifluoroborate salts. This was carried out  under the supervision of Professor Jonathan Percy and resulted in co-authoring a paper published in the Journal of Organic Chemistry (P. G. Wilson, J. M. Percy, J. M. Redmond and A. W. McCarter , 'Suzuki-Miyaura Coupling Reactions of Iodo(difluoroenol) Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient Temperatures'J. Org. Chem.201277 (15), 6384–6393.) 

Current Carnegie-Caledonian Scholars

The full list of current Carnegie-Caledonian scholars is available here.

Carnegie-Caledonian PhD Scholarships

The next deadline for applications is 28th February 2017.

To learn more about this scheme and how to apply, please visit Carnegie-Caledonian PhD Scholarships.