Organic anion formed by deprotonating a carbonyl (>C=O) compound
Resonance structures of an enolate anion.
In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl (RR'C=O) compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds.[1][2][3][4]
^Stolz, Daniel; Kazmaier, Uli (2010). "Metal Enolates as Synthons in Organic Chemistry". PATai's Chemistry of Functional Groups. doi:10.1002/9780470682531.pat0423. ISBN 978-0-470-68253-1.
^Hart, David J.; Ha, Deok Chan (1989). "The ester enolate-imine condensation route to .beta.-lactams". Chemical Reviews. 89 (7): 1447–1465. doi:10.1021/cr00097a003.
^Wu, George; Huang, Mingsheng (2006). "Organolithium Reagents in Pharmaceutical Asymmetric Processes". Chemical Reviews. 106 (7): 2596–2616. doi:10.1021/cr040694k. PMID 16836294.
^Curti, Claudio; Battistini, Lucia; Sartori, Andrea; Zanardi, Franca (2020). "New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems". Chemical Reviews. 120 (5): 2448–2612. doi:10.1021/acs.chemrev.9b00481. PMC 7993750. PMID 32040305.
In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl (RR'C=O) compounds. Rarely isolated, they are widely used...
the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation...
enantiomer. Lithium enolates are formed through deprotonation of a C−H bond α to the carbonyl group by an organolithium species. Lithium enolates are widely used...
case mediated by the enolate or the proton source. In the deprotonation of an unsymmetrical ketone, the kinetic product is the enolate resulting from removal...
quantitatively form the enolate of one partner, and the forward aldol reaction must be significantly faster than the transfer of the enolate from one partner...
In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or aldol (aldehyde + alcohol)...
or ketones. Aldol addition or aldolization refers to the addition of an enolate or enolation as a nucleophile to a carbonyl moiety as an electrophile....
enolizable (have an α-proton and be able to undergo deprotonation to form the enolate anion). There are a number of different combinations of enolizable and...
chemistry for a variety of oxidations, including alpha hydroxylation of enolates, epoxidation and aziridination of olefins, and other heteroatom transfer...
compounds that share the common functional group R3Si−O−CR=CR2, composed of an enolate (R3C−O−R) bonded to a silane (SiR4) through its oxygen end and an ethene...
because this species exists mainly as the monoenol CH3C(O)CH=C(OH)CH3. Its enolate is a common ligand in coordination chemistry. Ketones containing alkene...
reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated...
In this type of reaction, a nucleophile – such as an alcohol, amine, or enolate – displaces the leaving group of an acyl derivative – such as an acid halide...
peroxide, pyridine and hexamethylphosphoramide. Enolates can be oxidized by sulfonyloxaziridines. The enolate reacts by nucleophilic displacement at the electron...
important for enol- and enolate-based carbonyl chemistry as well. Chemical transformations affected by the conversion to either an enolate or an enol, in general...
in which context it is also known as Mander's reagent. When a lithium enolate is generated in diethyl ether or methyl t-butyl ether, treatment with Mander's...
deprotonated at the kinetic site. This enolate may then encounter other ketones and the thermodynamic enolate will form through the exchange of protons...
soluble in organic solvents and in alkaline water. It readily forms an enolate. The enolate forms a variety of metal complexes related to the metal acetylacetonates...
N-methyl-Δ1-pyrrolinium cation. The first addition is a Mannich-like reaction with the enolate anion from acetyl-CoA acting as a nucleophile towards the pyrrolinium cation...
initiator, it can replace some organotin compounds. It reacts with metal enolates, yielding enoxytriethylborates that can be alkylated at the α-carbon atom...
quality of the formyl center and the fact that the conjugate base, an enolate anion, delocalizes its negative charge. The formyl proton itself does not...
reaction is the addition of a two equivalents of nitric oxide onto an enolate, giving a diazeniumdiolate (also called a nitrosohydroxylamine). The product...
salt at –78 °C to give a chelated enolate as intermediate. While different metal salts can be used to form the enolate, the use of zinc chloride results...
relatively strong bases, such as alkoxides. Deprotonation gives a nucleophilic enolate, which can further react, e.g., the Claisen condensation and its intramolecular...
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