sodium periodate in water T=10°C; 1 h;

2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide in 1,4-dioxane; water T=20°C; 3 h;

1: potassium hydroxide; copper powder 2: diluted sulfuric acid View Scheme

sulfuric acid

potassium hydrogencarbonate in water 4 h; Ambient temperature;

1: (+)-6,6'-(((1R,2R,4R,5R)-bicyclo[2.2.2]octane-2,5-diylbis(azanediyl))bis(methylene))bis(2,4-di-tert-butylphenol); (CuOTf)2*C6H5CH3 / methanol / 40 °C / |Molecular sieve 2: hydrogen; palladium on activated charcoal / methanol / 20 °C / 760.05 Torr 3: 20 °C 4: hydrogen; palladium on activated charcoal / 20 °C / 760.05 Torr View Scheme