Oxidative Coupling of Enolates

Oxidative Coupling of Enolates

  • General Characteristics

Enolate species undergo dimerization under appropriately chosen oxidative conditions. Homo-coupling usually predominates, but there are successful examples of controlled hetero-coupling using carefully designed substrates.

  • General References

  • Reaction Mechanism

  • Examples

In 2007, MacMillan reported the remarkable catalytic enantioselective version of enolate coupling, the reactivity of which has been explained by SOMO (singly occupied molecular orbital)-activation mechanism.[1]


The application in the context of actinophyllic acid total synthesis.[2]


  • Experimental Procedure

  • Experimental Tips

  • References

[1] Jang, H.-Y.; Hong, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004. DOI: 10.1021/ja0719428 [2] Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568. doi: 10.1021/ja803158y

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