Lemieux-Johnson Oxidation

Schematic representation of the Lemieux-Johnson Oxidation.

Mechanism of the Lemieux-Johnson Oxidation

Mechanism of the Lemieux-Johnson Oxidation

Original publication	J. Org. Chem.. 1956, 21, 478.
Review	Comp. Org. Syn.. 1991, 7, 541.

Sample reactions

intermediate structure

2,6-Lutidine, OsO4, NaIO4

Dioxane , H2O

RT, 30 min, 86%

intermediate structure

intermediate structure

OsO4, NaIO4

Acetone, H2O

intermediate structure

intermediate structure

2,6-Lutidine, NaIO4, K2OsO2(OH)4

Dioxane , H2O

RT

intermediate structure

intermediate structure

OsO4, NaIO4

H2O, THF

70 °C, 18 h, 84%

intermediate structure

intermediate structure

HIO4, NaIO4, RuO2

H2O, t-BuOH

RT, 18 h, 72%

intermediate structure

intermediate structure

OsO4, NaIO4

H2O, THF

57% (2 steps)

intermediate structure

intermediate structure

OsO4, NaIO4

Dioxane , H2O

RT, ON, 79%

intermediate structure

intermediate structure

K2OsO2(OH)4, KIO4

H2O, THF

0 °C, 4 h, 62%

intermediate structure

intermediate structure

OsO4, NaIO4

Dioxane , H2O, t-BuOH

RT, 7 h, 85%

intermediate structure

intermediate structure

NMO, OsO4, KIO4

Acetone, H2O, t-BuOH

RT, 65 min, 89%

intermediate structure

intermediate structure

2,6-Lutidine, OsO4, NaIO4

Dioxane , H2O, t-BuOH

RT, 26 h, 96% (2 steps)

intermediate structure

intermediate structure

2,6-Lutidine, OsO4, NaIO4

Dioxane , H2O, t-BuOH

RT, 24 h, 67%

intermediate structure

intermediate structure

OsO4, NaIO4

75%

intermediate structure

intermediate structure

OsO4, NaIO4

70%

intermediate structure