Chiral Silanediols in Anion-Binding Catalysis


  • Support for this research has been provided by the OSU Department of Chemistry and Biochemistry and Donors of the American Chemical Society Petroleum Research Fund. We thank Dr. Judith Gallucci for expert crystallographic analysis.


original image

A perfect pair: Silanediols are effective catalysts for the addition of silyl ketene acetals to N-acylisoquinolinium ions. Importantly, this is the first example of a silanediol plausibly participating in anion-binding catalysis, a relatively new direction in the field of hydrogen-bond-donor catalysis. The chiral, enantiopure C2-symmetric silanediol 1 catalyzes enantioselective transformations.