I completed my undergraduate degree here at the University of Warwick. The course included a project whereby I was able to create a variety of possible anti-inflammatory compounds, two of which have been patented and are in pre-clinical trials. Following on from this I chose to undertake the AS:MIT course to further my knowledge of the analytical tools available in a research laboratory.
Investigating competition of phase transfer catalysts using chiral HPLC
Production of un-natural amino acids from basic starting materials using catalytic (<10 mol%) loading of a PTC (phase transfer catalyst) has long been studied. For this project a variety of quarternary ammonium salts were synthesised. The ee of the products is being determined by chiral HPLC. Synthesised compounds are completely characterised by HRMS, 1H/13C-NMR, IR, mpt, [α]D.
Example phase transfer catalysts used. Cinchonine derivatives shown using benzyl and methylanthracenyl directing groups (quinine derivatives also used)
Variable stereochemistry at the O-allyl position provides the enantioselective control of the product.
Reaction scheme used as a basis for the analysis. Benzyl bromide can also be substituted by a variey of
other alkylating agents including MeI which was also used.