Aliphatic C–H Bond Oxidation with Hydrogen
Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through
Torsional Effects
Posted on 2018-04-20 - 17:19
Substituted N-cyclohexyl amides undergo aliphatic
C–H bond oxidation with H2O2 catalyzed
by manganese complexes. The reactions are directed by torsional effects
leading to site-selective oxidation of cis-1,4-, trans-1,3-, and cis-1,2-cyclohexanediamides.
The corresponding diastereoisomers are unreactive under the same conditions.
Competitive oxidation of cis–trans mixtures of 4-substituted N-cyclohexylamides leads
to quantitative conversion of the cis-isomers, allowing
isolation and successive conversion of the trans-isomers
into densely functionalized oxidation products with excellent site
selectivity and good enantioselectivity.
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Milan, Michela; Bietti, Massimo; Costas, Miquel (2018). Aliphatic C–H Bond Oxidation with Hydrogen
Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through
Torsional Effects. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b00929
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AUTHORS (3)
MM
Michela Milan
MB
Massimo Bietti
MC
Miquel Costas