Synthesis, resolution and applications of 3,3'-disubstituted BIPHEP and BINAP derivatives in asymmetric organic synthesis

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The goal of this proposal is to develop new asymmetric catalysts and reagents that will provide products of reactions with high enantioselectivity. Compounds that are marketed as drugs that contain one or more stereogenic centres can exist as two enantiomers. It is important that chemists design new asymmetric catalysts that allows for the production of one enantiomer selectively over the other as each enantiomer can behave differently within a chiral environment like the human body. Thus in order to market a new drug containing stereogenic centres, each anantiomer must be synthesized independent of the other and tested separately for unwanted side effects. This is not an easy task as enantiomers have the same chemical and physical properties in a non-chiral environment (i.e in the laboratory where they are synthesized). Thus chemists must design new asymmetric catalysts that allow for the formation of one enantiomer over the other in the laboratory. The design of catalysts outlined in this proposal should allow for the production of enantiomers selectively. By having to avoid a resolution, the cost of making the drug should be lower and thus ultimately the consumer should pay less for their prescriptions. Thus this research could ultimately benefit anyone needing drugs that contain stereogenic centres.