Jacobsen epoxidation

The Jacobsen Epoxidation is a chemical reaction which allows enantioselective synthesis of epoxides from isolated alkenes.Ref|Zhang1990Ref|Jacobsen1991 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 maganese atom transfers an oxygen atom from chlorine bleach or similar oxidant. The reaction is named after its inventor, Eric Jacobsen, currently of Harvard University.

Several improved procedures have been developed.Ref|Jacobsen1994Ref|Chang1994Ref|Brandes1994

References

# Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. "J. Am. Chem. Soc." 1990, "112", 2801-2803. (DOI|10.1021/ja00163a052)
# Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. "J. Am. Chem. Soc." 1991, "113", 7063-7064. (DOI|10.1021/ja00018a068)
# Jacobsen, E. N. "et al." "Tetrahedron" 1994, "50", 4323.
# Chang, S.; Galvin, J. M.; Jacobsen, E. N. "J. Am. Chem. Soc." 1994, "116", 6937-6938. (DOI|10.1021/ja00094a059)
# Brandes, B. D.; Jacobsen, E. N. "J. Org. Chem." 1994, "59", 4378-4380. (DOI|10.1021/jo00095a009)

External links

* [http://www.organic-chemistry.org/namedreactions/jacobsen-katsuki-epoxidation.shtm Jacobsen Epoxidation]