Presentation: 2025 ND EPSCoR Annual conference 

October 21, 2025, NDSU Memorial Union, Fargo, North Dakota

Novel Methods for the Installation of All Carbon Quaternary Centers

Catalysis is one of the fundamental pillars of green chemistry by enhancing the efficiency and selectivity of the reactions while reducing the need for harsh reaction conditions and minimizing waste generation. It plays a crucial role in the synthesis of chiral tertiary and quaternary centers, which are key structural motifs in numerous natural products and bioactive molecules. However, steric repulsion between carbon substituents makes the construction of such quaternary centers particularly challenging. One of the most established approaches for the stereoselective synthesis of small chiral compounds is the conjugate addition of nucleophiles to electron-deficient α,β-unsaturated carbonyls. In this work, we have developed a chiral Lewis acid-mediated method for the highly selective addition of neutral carbon nucleophiles to β,β-disubstituted-α,β-unsaturated carbonyl compounds. This strategy enables the efficient formation of a single all-carbon quaternary center as well as two adjacent chiral quaternary centers with high selectivity. Results from these investigations will be presented.