Grant: Strategic Projects - Group

Catalytic methods afford energy efficient routes for the synthesis of complex molecules. Amines are critical building blocks for the assembly of a broad range of target compounds including alkaloid natural products, pharmaceuticals and agrochemicals. Often the required amine building blocks are chiral, meaning they have non-superimposable mirror images (enantiomers), and these enantiomers can have different properties when reacted with targeted biological receptors in human health treatments. Thus, the selective synthesis of enantiomeric amines and N-containing cyclic compounds (N-heterocycles) is an important aspect of daily production for the pharmaceutical industry. New methods to achieve the efficient syntheses of these small molecule building blocks can result in reduced waste production and cost savings during manufacture. The Schafer group has recently discovered a new family of catalysts for the efficient synthesis of chiral amines from simple amines and alkene feedstocks, in a 100% atom-economic reaction (there are no by-products in this reaction). This new reaction, the alpha-alkylation of amines, assembles the desired chiral amine products in only one step, with no by-products, by using a synthetic strategy that is complementary to traditional step-wise routes. A focused effort to realize the full potential of this new synthetic transformation and to extend academic achievements to small molecules of relevance to the pharmaceutical industry is supported by Boehringer Ingelheim Canada Ltd. This collaboration will exploit this emerging technology in the competitive manufacturing of required amine small molecules for the pharmaceutical industry. Using this catalytic approach, traditional multi-step syntheses can be reduced to one atom-economic, catalytic step. The newly developed catalysts take advantage of the low toxicity of tantalum, a metal frequently used in medical implants. Thus, this proposal also addresses green manufacturing approaches for the environmentally friendly synthesis of these critical building blocks for application in the pharmaceutical industry.