Influence of base and structure in the reversible covalent conjugate addition of thiol to polycyclic enone scaffolds.

The energetics of thiol addition and elimination reactions to bicyclic enones derived from an indole core structure were explored using (1)H NMR and density functional theory (DFT) calculations. The agreement between experiment and theory is excellent, and the combined results reveal that even minor changes in the conformation of the enone, substituents on… CONTINUE READING