Jacobsen epoxidation
The Jacobsen epoxidation, sometimes also referred to as Jacobsen-Katsuki epoxidation is a chemical reaction which allows enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes. It is complementary to the Sharpless epoxidation (used to form epoxides from the double bond in allylic alcohols). The Jacobsen epoxidation gains its stereoselectivity from a C2 symmetric manganese(III) salen-like ligand, which is used in catalytic amounts. The manganese atom transfers an oxygen atom from chlorine bleach or similar oxidant. The reaction takes its name from its inventor, Eric Jacobsen, with Tsutomu Katsuki sometimes being included. Chiral-directing catalysts are useful to organic chemists trying to control the stereochemistry of biologically active compounds and develop enantiopure drugs.
| Jacobsen epoxidation | |
|---|---|
| Named after | Eric N. Jacobsen |
| Reaction type | Ring forming reaction |
| Identifiers | |
| Organic Chemistry Portal | jacobsen-katsuki-epoxidation |
| RSC ontology ID | RXNO:0000686 |
Several improved procedures have been developed.
A general reaction scheme follows: