Categories: C-O Bond Formation > Synthesis of esters >

Redox Esterification

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Name Reaction

Tishchenko Reaction

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Recent Literature

Homoenolates are generated by reaction of N-heterocycle carbenes with enals, leading to carbon-carbon bond formation or activated carboxylates depending on the used base. The design of a new triazolium precatalyst enabled the catalytic, atom-economical redox esterification of enals.
S. S. Sohn, J. W. Bode, Org. Lett., 2005, 7, 3873-3876.

N-Heterocyclic carbenes are effective catalysts for an Umpolung reaction of α,β-unsaturated aldehydes. The generated homoenolate species can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile to form a saturated ester.
A. Chan, K. A. Scheidt, Org. Lett., 2005, 7, 905-908.

The catalytic generation of activated carboxylates from epoxyaldehydes enables a direct, anti-selective, convenient and mild synthesis of β-hydroxyesters.
K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc., 2004, 126, 8126-8127.