To validate the kinetic feasibility of the R-enantioselective reaction, we performed QM/MM calculations, using the most populated snapshot based on Boltzmann population distribution * , followed by potential energy scan along the H-abstraction pathway. Furthermore, since recent investigations revealed that the pristine oxidant HM1 exhibits two-state reactivity (doublet and sextet spins) in its gas phase reaction with methane, we investigate the reactivity of the two spin states. Our QM/MM calculations, in Figures and, show that the ground state of HM1 is the doublet state. The reaction barrier is also lower than in the sextet state and the reaction is hence spinselective (>99%). Clearly therefore the box modifies the intrinsic properties of the captive HM1. difference, the R/S ratio at 298.15 K, corresponds to 159:1 for R/S enantio-selectivity of the Tetralol (see SI, Figure ). Clearly the cage modifies both the reactivity and enantioselectivity of HM1.