Jacobsen epoxidation

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The Jacobsen Epoxidation is a chemical reaction which allows enantioselective synthesis of epoxides from isolated alkenes.[1][2] 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 complex, which is used in catalytic amounts. The reaction is named after its creator, Eric Jacobsen of Harvard University.

Several improved procedures have been developed.[3][4][5]


  1. ^ Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803. (doi:10.1021/ja00163a052)
  2. ^ 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)
  3. ^ Jacobsen, E. N. et al. Tetrahedron 1994, 50, 4323.
  4. ^ Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937-6938. (doi:10.1021/ja00094a059)
  5. ^ Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (doi:10.1021/jo00095a009)

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