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Further Information

Related Reactions
Aldol Addition
Robinson Annulation
Synthesis of enones

Aldol Condensation

In some cases, the adducts obtained from the Aldol Addition can easily be converted (in situ) to α,β-unsaturated carbonyl compounds, either thermally or under acidic or basic catalysis. The formation of the conjugated system is the driving force for this spontaneous dehydration. Under a variety of protocols, the condensation product can be obtained directly without isolation of the aldol.

The aldol condensation is the second step of the Robinson Annulation.

Mechanism of the Aldol Condensation

For the addition step see Aldol Addition

Recent Literature

An Efficient Method for the Selective Iodination of α,β-Unsaturated Ketones
Z. Wang, G. Yin, J. Qin, M. Gao, L. Cao, A. Wu, Synthesis, 2008, 3565-3568.

CBr4 as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones
I. Kazi, S. Guha, G. Sekar, Org. Lett., 2017, 19, 1244-1247.

One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds
M. Sugiura, Y. Ashikari, M. Nakaijima, J. Org. Chem., 2015, 80, 8830-8835.

Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates
J. K. Mansaray, J. Sun, S. Huang, W. Yao, Synlett, 2019, 30, 809-812.

Synthesis of Cyclopentenones with C4-Quaternary Stereocenters via Stereospecific [3,3]-Sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids
W. Zhou, A. Voituriez, J. Am. Chem. Soc., 2021, 143, 17348-17353.

Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis
L. Hou, W. Huang, X. Wu, J. Qu, Y. Chen, Org. Lett., 2022, 24, 2699-2704.

Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines
J. Zhou, B. List, J. Am. Chem. Soc., 2007, 129, 7498-7499.

Selective Macrocycle Formation in Cavitands
J.-M. Yang, Y. Yu, J. Rebek Jr., J. Am. Chem. Soc., 2021, 143, 2190-2193.