Highly Enantioselective Oxidation of Nonactivated Aliphatic C-H Bonds with Hydrogen Peroxide Catalyzed by Manganese Complexes.

ABSTRACT: Monosubstituted cycloalkanes undergo regio- and enantioselective aliphatic C-H oxidation with H₂O₂ catalyzed by biologically inspired manganese catalysts. The reaction furnishes the corresponding ketones resulting from oxidation at C3 and C4 methylenic sites (K₃ and K₄, respectively) leading to a chiral desymmetrization that proceeds with remarkable enantioselectivity (64% ee) but modest regioselectivity at C3 (K₃/K₄ ≈ 2) for tert-butylcyclohexane, and with up to 96% ee and exquisite regioselectity toward C3 (up to K₃/K₄ > 99) when N-cyclohexylalkanamides are employed as substrates. Efficient H₂O₂ activation, high yield, and highly enantioselective C-H oxidation rely

SUBMITTER: Milan M 

PROVIDER: S-EPMC5364455 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature