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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.
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General References
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Reaction Mechanism
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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]
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Experimental Procedure
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Experimental Tips
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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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Related Reactions
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Related Books
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External Links