In summary, statistical and computational methods enable identification of the key parameters controlling both product yield and enantioselectivity in the desymmetrization of cyclohexane scaffolds via oxidation of methylenic units with chiral manganese catalysts. Based on an extended experimental dataset, internally validated models for carboxylic acids, substrates and catalyst have been developed. The logistic regression model for the acids identifies that small and electron-rich acids maximize the probability of providing a high reaction yield. The predictive MLR model found for the substrates correlates basicity and size of the cyclohexane substituents with enantioselectivity.