Organocatalytic synthetic methods are attractive alternatives to transition metal catalysis.  Small organic molecule catalysts not only offer complementary reactivity patterns to metals, they often benefit from being less expensive, more robust, and more environmentally friendly.  Ureas, and other hydrogen bond donors (HBD), are one particularly attractive family of organic catalysts capable of effecting transformations through hydrogen bonding interactions.  Despite the undeniable promise of HBD catalysis, challenges, such as high catalyst loadings and limited reactivity patterns, limit its widespread use in academia and industry.  This work will present recent advances from the Mattson group in the design and utility of HBD catalysts.  In particular, internal Lewis acid-assisted ureas and silanediols will be discussed with a focus on new patterns of reactivity and the synthesis of these unique HBD catalyst frameworks.

Hydrogen bond donor organic catalysts for the discovery of new reactivity patterns

246th National Meeting (2013)

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