Sharpless Epoxidation

Schematic representation of the Sharpless Epoxidation.

Mechanism of the Sharpless Epoxidation

Mechanism of the Sharpless Epoxidation

Original publication	J. Am. Chem. Soc.. 1980, 102, 5974.
Reviews	Chem. Rev.. 1989, 89, 431. Comp. Org. Syn.. 1991, 7, 389. Org. React.. 1996, 48, 1. Synthesis. 1986, 0, 89. Top. Curr. Chem.. 1993, 164, 63.

Sample reactions

intermediate structure

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

4 Å MS

CH2Cl2

-20 °C, 5 h, 75%

intermediate structure

intermediate structure

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

4 Å MS

CH2Cl2

-23 °C, 20.5 h, 90%

intermediate structure

intermediate structure

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

CH2Cl2

-23 °C, , 92%

intermediate structure

intermediate structure

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

4A MS

CH2Cl2

-20 °C, 12.5 h, 80%

"95% ee"

intermediate structure

intermediate structure

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

4A MS

CH2Cl2

-30 °C to RT, 7.5 h, 98%

"91% ee"

intermediate structure