Exploration into Rotationally Restricted N-Alkyl 2-Quinolones
Chemistry and Biochemistry
Axially chiral molecules are an interesting class of compounds whose chirality stems from an inability to rotate around a central bond. As chiral agents, these species have potential uses as asymmetric ligands, chiral derivatizing agents, or as chiral building blocks for the preparation of more complex targets. We have identified a synthetically accessible N-alkyl 2-quinolone, which exhibits hindered rotation. Using computational analysis, the rotational barriers for a series of more highly substituted analogues were calculated and a quinolone with an energetic barrier that is predicted to be high enough to lead to axial chirality was identified. A synthetic pathway to this candidate is being explored.