Hydrogen-bonds are effective forces for activating reactants and orienting them in chiral environments. Tailoring these properties for synthetic utility has resulted in the emergence of hydrogen-bonds as powerful control elements in asymmetric catalysis. Principles of H-bond donor catalyst design has led to our pursuit of thiosquaramides as bifunctional catalysts. Preparation of bifunctional thiosquaramides will be discussed and their application in making chiral barbiturates demonstrated. H-bonding catalysis without bifunctionality provides opportunities to render other reactions asymmetric. The catalytic performance of new H-bonding scaffolds without requisite bifunctionality will be discussed and the translation of these results to asymmetric synthesis presented.

Development of hydrogen-bond donor catalysts for asymmetric C-C bond formation

253rd National Meeting (2017)

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