Understanding Catalytic Enantioselective C-H Bond Oxidation at Nonactivated Methylenes Through Predictive Statistical Modeling Analysis.

Enantioselective C(sp)-H bond oxidation is a powerful strategy for installing functionality in C(sp)-H rich molecules. Site- and enantioselective oxidation of strong C-H bonds in monosubstituted cyclohexanes with hydrogen peroxide catalyzed by aminopyridine manganese catalysts in combination with alkanoic acids has been recently described. Mechanistic uncertainties and nonobvious enantioselectivity trends challenge development of the full potential of this reaction as a powerful synthetic tool.