The fast growing need of societally relevant enantiopure molecules, such as pharmaceuticals and agrochemicals, requires advancements in enantioselective catalysis. Thioureas, squaramides and silanediols are several typical families of hydrogen-bond-donor (HBD) catalysts with unique abilities to promote reactions through anion-binding interactions. In this study, we have successfully determined the association constants of select silanediols, thioureas, and squaramides with various anions via <sup>1</sup>H NMR, UV-vis, and fluorescence titration experiments. In addition, the catalytic activity of the same HBDs was explored in several enantioselective transformations, such as the Mannich reaction of silyl ketene acetals with <i>N</i>-acylisoquinolines, the addition of silyl ketene acetals to benzopyrylium triflates, and the Friedel-Crafts alkylation reactions of indoles with alkylidene malonates. Our studies not only provide valuable structure-activity relationships of several HBDs in terms of anion recognition ability and catalytic ability for the first time, they also generate insightful information applicable to the design of new catalysts and reactions in the field of hydrogen-bond-donor catalysis.

Anion recognition and catalytic ability of select chiral silanediols, thioureas, and squaramides

256th National Meeting (2018)

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