Enantioselective syn Hydration of Enones in Water Using a DNA-Based Catalyst

Significance

In this paper, the authors report the first non-enzymatic hydration of α,β-unsaturated ketones in water, which proceeds in an enantio­selective (up to 82% ee) and diastereospecific fashion (exclusive syn addition). The catalytic ­system consists of st-DNA (salmon testes DNA, approximately 2000 base pairs long) and a copper complex bound by non-covalent interactions (ligand L₁ provided the optimum results). The individual components (DNA, ligand, Cu^²+) have specific functions, which are synergistic; DNA serves as a chiral inductor, the presence of copper is crucial for the catalysis to occur, and the ligand tunes the interactions leading to higher reactivity and enantioselectivity.