Upjohn Dihydroxylation

Schematic representation of the Upjohn Dihydroxylation.

Mechanism of the Upjohn Dihydroxylation

Mechanism of the Upjohn Dihydroxylation

Original publication	Tetrahedron Lett.. 1976, 17, 1973.
Review	Chem. Rev.. 1980, 80, 187.

Sample reactions

intermediate structure

NMO, OsO4

Acetone, H2O, t-BuOH

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O

RT, 6 h, 57%

intermediate structure

intermediate structure

NMO, OsO4

H2O, t-BuOH, THF

40 h

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O, i-PrOH

RT, 15 h, 66%

intermediate structure

intermediate structure

NMO, OsO4

H2O, THF

RT, 8 h

intermediate structure

intermediate structure

NMO, OsO4

H2O, t-BuOH, THF

RT, 2 h, 69%

intermediate structure

intermediate structure

NMO, OsO4

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O

RT, 45 min, 76%

"Cristallized thrice to >99:01 er."

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O, THF

0 °C to RT, 2 h

intermediate structure

intermediate structure

NMO, OsO4

H2O, t-BuOH, THF

RT, 3 d, 64%

"Also isolated was the C-1 epimer (23 % yield)."

intermediate structure

intermediate structure

NMO, OsO4

Acetone, H2O

92%

intermediate structure

intermediate structure

NMO, OsO4

H2O, t-BuOH, THF

RT, 16 h

intermediate structure

intermediate structure

NMO, OsO4

H2O, t-BuOH, THF

RT, 12 h

intermediate structure