Sharpless Asymmetric Dihydroxylation

Mechanism of the Sharpless Asymmetric Dihydroxylation

Original publication	J. Am. Chem. Soc.. 1988, 110, 1968. J. Am. Chem. Soc.. 1999, 121, 9967.
Reviews	Chem. Rev.. 1994, 94, 2483. Org. React.. 2005, 66, 109.

Sample reactions

AD-mix B, MsNH2

t-BuOH

0 °C, 12 h, 88%

AD-mix B

0 °C to RT, , 89%

K2CO3, K3Fe(CN)6, K2OsO2(OH)4, DHQ-PHN

t-BuOH

0 °C, 11 h, 98%

K2CO3, MsNH2, K3Fe(CN)6, K2OsO2(OH)4, (DHQD)2PHAL

H2O, t-BuOH

t-BuOOH, Ti(Oi-Pr)4, (+)-DET

4 Å MS

CH2Cl2

-23 °C, 20.5 h, 91%

AD-mix B, MsNH2

H2O, t-BuOH, TBME

12 °C, 40 h, 55%

MsNH2, AD-mix A

H2O, t-BuOH

94%

AD-mix B

H2O, t-BuOH

0 °C, 42 h, 100%

">99:01 e.r."

K2CO3, MsNH2, K3Fe(CN)6, K2OsO2(OH)4, (DHQD)2PHAL

H2O, t-BuOH

0 °C, 15h, 61%

"97% ee"

K2CO3, K3Fe(CN)6, K2OsO2(OH)4, (DHQD)2Pyr

H2O, t-BuOH

0 °C, 7 h, 96%

"86:14 d.r."