Upjohn Dihydroxylation

Schematic representation of the Upjohn Dihydroxylation.
Mechanism of the Upjohn Dihydroxylation
Mechanism of the Upjohn Dihydroxylation
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