Applications of masked acyl cyanides - bridging synthesis and computational chemistry | Poster Board #1622

The Pigza research group focuses on the theme of noncovalent interactions as they are at the core of asymmetric catalysis and ultimately determine the fate of reactions. Masked acyl cyanide (MAC) reagents contain a weakly acidic methine hydrogen that can be activated by a mild base, making them prime for the study of noncovalent interactions in a variety of nucleophilic addition reactions including organocatalyzed reactions. Adducts can then be unmasked in a later step, revealing an ester, amide, or carboxylic acid functional group handle. This presentation will summarize three aspects of our research projects on MAC reagents: 1) their synthesis with various protecting groups, 2) their use as oxidation state three nucleophilic equivalents in reactions, and 3) the complementary computational study using density functional theory to better understand the relevant noncovalent interactions.