Anion-binding catalysis is emerging as a fruitful new direction in the field of hydrogen bond donor catalysis. Processes under the influence of anion-binding catalysis can benefit from reaction rate enhancement, high levels of stereocontrol, and unique bond-forming events that are inaccessible with other types of catalysis. At the onset of our investigations, ureas and related thioureas were the only known enantioselective anion-binding catalysts. We reasoned silanediols may operate as an entirely new family of anion-binding catalysts that would enable reactivity patterns inaccessible to (thio)ureas. Based upon recent discoveries made in our laboratory, we are excited to report the feasibility of enantioselective silanediol anion-binding catalysis in asymmetric N-acyl Mannich reactions between N-acylisoquinoliniums and silyl ketene acetals. Importantly, the success of this work emerged from our synthesis of the first enantiopure silanediol catalyst. Details surrounding the preparation of the enantiopure silanediols and insight into their plausible mode of action will be discussed.

Chiral silanediols in anion-binding catalysis

247th National Meeting (2014)

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