Lemieux-Johnson Oxidation

Schematic representation of the Lemieux-Johnson Oxidation.
Mechanism of the Lemieux-Johnson Oxidation
Mechanism of the Lemieux-Johnson Oxidation
Sample reactions
intermediate structure
OsO4, NaIO4, 2,6-Lutidine
Dioxane , H2O
RT, 30 min, 86%
intermediate structure
intermediate structure
OsO4, NaIO4
Acetone, H2O
intermediate structure
intermediate structure
K2OsO2(OH)4, NaIO4, 2,6-Lutidine
Dioxane , H2O
RT
intermediate structure
intermediate structure
OsO4, NaIO4
THF, H2O
70 °C, 18 h, 84%
intermediate structure
intermediate structure
RuO2, HIO4, NaIO4
t-BuOH, H2O
RT, 18 h, 72%
intermediate structure
intermediate structure
OsO4, NaIO4
THF, H2O
57% (2 steps)
intermediate structure
intermediate structure
OsO4, NaIO4
Dioxane , H2O
RT, ON, 79%
intermediate structure
intermediate structure
K2OsO2(OH)4, KIO4
THF, H2O
0 °C, 4 h, 62%
intermediate structure
intermediate structure
OsO4, NaIO4
Dioxane , t-BuOH, H2O
RT, 7 h, 85%
intermediate structure