As a substrate that can be used to explore reactivity and selectivity, we chose the conversion of Tetralin to Tetralol (Figure ), which involves both C-H hydroxylation and enantio-selectivity of the product. Thus, (R)-1-Tetralol is extensively used to treat several disorders such as obsessive-compulsive disorder, post-traumatic stress, premenstrual dysphoric disorder, and social anxiety . Can the chosen cage produce (R)-1-Tetralol? Can it produce, on demands, also (S)-1-Tetralol?