Jacobsen-Katsuki epoxidation

The Jacobsen epoxidation involves the enantioselective transformation of cis-substututed alkenes to epoxides using a manganese-salen complex as a catalysts.

 

Suggested mechanism:

Review (mechanistic studies):

The Jacobsen-Katsuki Epoxidation and Its Controversial Mechanism.
Torsten Linker Angew. Chem. Int. Ed.199736, 2060.

Further reading:

Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes.

Wei Zhang, Jennifer L. Loebach, Scott R. Wilson, and Eric N. Jacobsen
J. Am. Chem. Soc.1990; 112(7) pp 2801 – 2803.

Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane.
Eric N. Jacobsen, Wei Zhang, Alexander R. Muci, James R. Ecker, and Li Deng
J. Am. Chem. Soc.; 1991; 113(18) pp 7063 – 706.

Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins.
Bridget D. Brandes and Eric N. Jacobsen
J. Org. Chem.; 1994; 59(16) pp 4378 – 4380.