Sharpless Asymmetric Dihydroxylation

Schematic representation of the Sharpless Asymmetric Dihydroxylation.
Mechanism of the Sharpless Asymmetric Dihydroxylation
Mechanism of the Sharpless Asymmetric Dihydroxylation
Sample reactions
intermediate structure
AD-mix B, MsNH2
t-BuOH
0 °C, 12 h, 88%
intermediate structure
intermediate structure
AD-mix B
0 °C to RT, , 89%
intermediate structure
intermediate structure
K2CO3, K3Fe(CN)6, K2OsO2(OH)4, DHQ-PHN
t-BuOH
0 °C, 11 h, 98%
intermediate structure
intermediate structure
K2CO3, MsNH2, K3Fe(CN)6, K2OsO2(OH)4, (DHQD)2PHAL
H2O, t-BuOH
intermediate structure
intermediate structure
t-BuOOH, Ti(Oi-Pr)4, (+)-DET
CH2Cl2
-23 °C, 20.5 h, 91%
intermediate structure
intermediate structure
AD-mix B, MsNH2
H2O, t-BuOH, TBME
12 °C, 40 h, 55%
intermediate structure
intermediate structure
MsNH2, AD-mix A
H2O, t-BuOH
94%
intermediate structure