Office of Undergraduate Research

Synthesis of aldehydes bearing quaternary carbon centers via the Tsuji-Trost allylation

This project focuses on the field of synthetic methodology, specifically the use of asymmetric catalysis for the creation of molecules bearing quaternary stereocenters (ubiquitous in natural products having beneficial medical properties). The objective is to synthesize the product with the highest possible yield and enantiomeric excess (ee) value. This would involve carrying out the Pd catalysed Tsuji-Trost allylation on the allyl enol carbonates made from 3-hydroxy aryl acrylates. Working with metal catalysts requires proficiency in the use of Schlenk techniques and in the use of a glove box (necessary for carrying out air and moisture sensitive reactions). NMR and mass spectroscopy is routinely used for compound identification. In addition, the HPLC instrument is required in order to obtain ee values of the aldehyde products.

Tasks and responsibilities: