17716-05-1Relevant articles and documents
Aliphatic C-H Bond Oxidation with Hydrogen Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through Torsional Effects
Milan, Michela,Bietti, Massimo,Costas, Miquel
supporting information, p. 2720 - 2723 (2018/05/22)
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.
Stereoselective hydride reductions of cyclic N-diphenylphosphinyl imines. Highly diastereoselective syntheses of protected primary amines
Hutchins,Adams,Rutledge
, p. 7396 - 7405 (2007/10/03)
Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.