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Organic anion formed by deprotonating a carbonyl (>C=O) compound
In organic chemistry, enolates are the organic anions derived from the deprotonation of carbonyl (RR'C=O) compounds. Rarely isolated, they are widely used
Enolate
Chemical reaction
substitution of an α-hydrogen by an electrophile through either an enol or enolate ion intermediate. Because their double bonds are electron rich, enols behave
Carbonyl α-substitution reaction
Carbonyl_α-substitution_reaction
Chemical reaction
using a lithium enolate compared to 97:3 using a dibutylboron enolate. Where the counterion determines stereoinduction strength, the enolate isomer determines
Aldol_reaction
Chemical compounds containing C–Li bonds
kinetics studies of LDA-mediated reactions suggest that lower aggregates of enolates do not necessarily lead to higher reactivity. Also, some Lewis bases increase
Organolithium_reagent
Organic compound with a C=C–OH group
are stable compounds. However, deprotonation of organic carbonyls gives enolate anions, which are important in organic reaction strategies as a strong
Enol
Type of chemical reaction
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)
Aldol_condensation
Compound derived from an acid
tertiary alcohols. Esters also react readily with enolates. In the Claisen condensation, an enolate of one ester (1) will attack the carbonyl group of
Ester
Chemical reaction
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
Claisen_condensation
Organic compound with formula (CH3CO)2O
(CH3CO)2O + H2O → 2 CH3COOH Acetic anhydride forms the enolate in the presence of acetate as base. The enolate can be trapped by condensation with benzaldehyde
Acetic_anhydride
Chemical compound
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
Methyl_cyanoformate
Reaction in organic chemistry
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
Michael_addition_reaction
Class of chemical compounds
analogues to enolates, form by treating imines with strong bases such as LiNR2: RN=C(CH2R')R + LiN(iPr)2 → RN=C(CHLiR')R + HN(iPr)2 These aza enolates are highly
Enamine
Class of organosilicon compounds of the form R3Si–O–CR=CR2
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
Silyl_enol_ether
Type of aldol condensation reaction
cannot form an enolate, and the benzaldehyde is much more electrophilic than any unenolized acetophenone in solution. Therefore, the enolate formed from
Self-condensation
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
Thermodynamic and kinetic reaction control
Thermodynamic_and_kinetic_reaction_control
Chemical compound
that is used to synthesize vinyl triflates from the corresponding ketone enolates or dienolates. It was first reported in 1992 by Daniel Comins. The vinyl
Comins'_reagent
Organic reaction
form β-hydroxy-esters: The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. The reaction
Reformatsky_reaction
Chemical reaction
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
Claisen_rearrangement
Pyrophoric liquid
initiator, it can replace some organotin compounds. It reacts with metal enolates, yielding enoxytriethylborates that can be alkylated at the α-carbon atom
Triethylborane
Organic chemical reaction
withdrawing group. Z must be powerful enough to facilitate deprotonation to the enolate ion even with a mild base. Using a strong base in this reaction would induce
Knoevenagel_condensation
Chemical reaction
base first converts the ketone or ester into its corresponding enolate. Then, the enolate anion as a nucleophile attacks the oxygen atom of the oxaziridine
Davis_oxidation
Chemical reaction
form a metal-stabilized enolate, which then attacks the tethered alkyne and transfers the metal cation. An early example of enolate activation was reported
Conia-ene_reaction
Chemical compound
Me(Et)C=NNH2 + H2O In the Davis oxidation, N-sulfonyloxaziridines oxidize enolates to acyloins with high chiral induction, better than (e.g.) MoOPH. Chiral
Oxaziridine
Chemical compound
deprotonated at the kinetic site. This enolate may then encounter other ketones and the thermodynamic enolate will form through the exchange of protons
Lithium_diisopropylamide
Chemical compound
replaced by DMPU. It is an electrophilic source of oxygen that reacts with enolates and related structures, and thus can be used for alpha-hydroxylation of
MoOPH
Prefix in organic chemistry nomenclature
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
Locant
Process of addition of silyl group(s) to compounds
groups to solids. Silyl groups are commonly used for: alcohol protection, enolate trapping, gas chromatography, electron-impact mass spectrometry (EI-MS)
Silylation
Organic compounds of the form >C=O
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
Ketone
Chemical compound
5-diketopiperazine ring by enolate acylation was used in the construction of the 2,5-diketopiperazine ring in 11 by intramolecular cyclization of the enolate of 10 onto
2,5-Diketopiperazine
used for the acylation of alcohols and the rearrangement of O-acylated enolates. Due to the need for an enantioselective version of this catalyst, Gregory
Fu's_Planar_DMAP
Chemical reaction
peroxide enolate (Figure 3). All of the reactants associate with the polyleucine catalyst prior to reaction to form the hydroperoxide enolate intermediate
Juliá–Colonna_epoxidation
Chemical compound
is used in asymmetric synthesis for example in the formation of boron enolates in the aldol reaction. Organic Syntheses, Coll. Vol. 8, p.339 (1993); Vol
Dibutylboron trifluoromethanesulfonate
Dibutylboron_trifluoromethanesulfonate
Chemical compound
is readily substituted by nucleophiles such as amines, phenoxides, and enolates, giving sulfonamides, aryl nonaflates, and alkenyl nonaflates, respectively
Perfluorobutanesulfonyl fluoride
Perfluorobutanesulfonyl_fluoride
Toxic, waxy organic compound
converted to the alkene bornylene. Camphor forms an enolate when treated with sodium hydride. The enolate condenses with esters to give 1,3-diketones. In
Camphor
Enzyme family
power of NADPH to perform a hydride shift on the double carbon bond in the ring causing enolate formation and subsequent tautamerization to form DHT.
5α-Reductase
Chemical reaction discovered by and named after W. Baker and K. Venkataraman
with base to form 1,3-diketones. This rearrangement reaction proceeds via enolate formation followed by acyl transfer. It is named after the scientists Wilson
Baker–Venkataraman rearrangement
Baker–Venkataraman_rearrangement
Chemical compound
dibenzylideneacetone. Because relatively weak bases such as NaOH make very little of the enolate ion at equilibrium, there is still a lot of unreacted base left in the
Benzylideneacetone
Conjugate base of an alcohol
Transition metal alkoxides are widely used for coatings and as catalysts. Enolates are unsaturated alkoxides derived by deprotonation of a C−H bond adjacent
Alkoxide
Process that results in the interconversion of chemical species
1002/0471264180. ISBN 978-0-471-26418-7. Hunt, Ian. "Chapter 18: Enols and Enolates — The Michael Addition reaction". University of Calgary. Brückner, p. 580
Chemical_reaction
Chemical reaction for synthesizing C–N bonds
in order to generate the thiophenol from the corresponding aryl halide. Enolates and other similar carbon nucleophiles can also be coupled to produce α-aryl
Buchwald–Hartwig_amination
Chemical compound
configuration) in the β-lactam a chiral auxiliary is used in the enolate synthesis. The enolate synthesis starts from glycolic acid. The hydroxyl group is protected
Ojima_lactam
Chemical reaction
reaction of enolates has been the main focus of the field. Both A. G. Myers and D. A. Evans developed asymmetric alkylation reactions for enolates. The apparent
Enders SAMP/RAMP hydrazone-alkylation reaction
Enders_SAMP/RAMP_hydrazone-alkylation_reaction
reaction sequence in many examples starts from conversion of a ketone into an enolate by action of lithium diisopropylamide (LDA), to which a suitable aldehyde
Aldol–Tishchenko_reaction
Ionic compound with the formula [(H3C–)2N–CH2]I
dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2. Enolates, silyl enol ethers, and even more acidic ketones undergo efficient
Eschenmoser's_salt
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
strong base such as lithium diisopropylamide selectively furnishes the (Z)-enolate, which can undergo stereoselective alkylation. Alkylation of an oxazolidinone
Chiral_auxiliary
Chemical reaction
Favorskii rearrangement begins when an enolate forms on the side of the ketone away from the chlorine atom. This enolate cyclizes to a cyclopropanone intermediate
Favorskii_rearrangement
Organic compound (C6H5OH)
number of resonance structures available to phenoxide compared to acetone enolate seems to contribute little to its stabilization. However, the situation
Phenol
Chemical reaction
followed by trapping of the resulting enolate with an electrophile at the α-position. When the nucleophile is an enolate and the electrophile a proton, the
Vicinal_difunctionalization
Chemical reaction
six-membered chair-like transition state, coordinating metal cations to both enolate oxygens and the electrophile, which explains its high anti‑stereoselectivity
Ivanov_reaction
Chemical reaction
carbonyl compounds through the intermediacy of a hypervalent iodine(III) enolate species. This electrophilic intermediate may be attacked by a variety of
Carbonyl oxidation with hypervalent iodine reagents
Carbonyl_oxidation_with_hypervalent_iodine_reagents
Use of squaramides as hydrogen-bond catalyst to accelerate reactions
Michael acceptors, and epoxides. The nucleophile can be nitroalkanes, enolates, and even phenols (resulting in electrophilic aromatic substitution). Subsequent
Squaramide_catalysis
nucleophiles can be sodium amide, an alkoxide or a carbon nucleophile such as an enolate. In contrast to regular nucleophilic aromatic substitution, deactivating
Radical-nucleophilic aromatic substitution
Radical-nucleophilic_aromatic_substitution
Organic compound containing the functional group R–CH=O
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
Aldehyde
Chemical reaction
Summary of enolate and nitronate nucleophilic additions to imines and aldehydes/ketones.
Nitro-Mannich_reaction
American organic chemist
stereocenters. Specifically, he has focused on the allylic alkylation of enolates, developing an enantioselective variant in 2004. Stoltz received undergraduate
Brian_Stoltz
Chemical reaction
needed] One proposal: Enolate formation: Ester is deprotonated at the α-position, to give enolate anion. CH₂ insertion: Enolate reacts with dihalomethane
Kowalski_ester_homologation
Chemical reaction in organic chemistry
the thermodynamic enolate. Alternatively, the regioselectivity is often controlled by using a β-diketone or β-ketoester as the enolate component, since
Robinson_annulation
American chemist
Technology for graduate school, where he worked with Herbert O. House on enolate anions, the Mannich reaction, and the Robinson annulation. Trost graduated
Barry_Trost
Chemical reaction
by 1010-1017, the anionic oxy-Cope rearrangement. The formation of an enolate renders the reaction irreversible in most cases. Sigmatropic rearrangements
Oxy-Cope_rearrangement
Class of enzymes
hydride at 3.4 Å to the Cδ, compared with 4.0 Å to the Cβ (not shown). The enolate intermediate discussed earlier is stabilized by residues additional hydrogen
2,4_Dienoyl-CoA_reductase
Chemical reaction
α-carbon. This carbon is preferred over the methyl carbon because the formed enolate is conjugated and thus resonance stabilized. The carbon then undergoes
Acetoacetic_ester_synthesis
Type of organic chemical compound
deprotonated anions of ynols are known as ynolates, the triple-bond analogues to enolates. Alkynols may be formed by the alkynylation of carbonyl compounds, usually
Alkynol
condensation at the KS by (5) decarboxylation and (6) nucleophilic attack of the enolate at the carbonyl carbon of the acyl group, (7) Reduction of the keto group
Fatty-acyl-CoA_synthase
transformations in this sequence are a Chan rearrangement and a sulfonyloxaziridine enolate oxidation. It was envisaged that Taxol (51) could be accessed through tail
Holton_Taxol_total_synthesis
Molecule
brominated in the alpha-position by NBS using acid catalysis. The reaction of enolates, enol ethers, or enol acetates with NBS is the preferred method of α-bromination
N-Bromosuccinimide
Chemical compound
Adamantanone and some related polycyclic ketones, are reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation
Adamantanone
Chemical reaction
synthesis is related to the Knoevenagel condensation. In the second step the enolate displaces an alkyl halogen in a nucleophilic aliphatic substitution. In
Feist–Benary_synthesis
Chemical reaction used in organic chemistry
elimination reaction to lose a β-hydrogen. Subsequent tautomerization of the enolate produces the cyclopentenone product. As noted above, variants that deviate
Nazarov_cyclization
Organic reaction
original reaction consisted of a nucleophilic aliphatic substitution of the enolate of ethyl cyclohexanone-2-carboxylate with 1,4-diiodobutane and sodium hydride
Dowd–Beckwith ring-expansion reaction
Dowd–Beckwith_ring-expansion_reaction
Ionic compound made of a C2H5–O anion and a sodium cation
may either deprotonate the α-position of an ester molecule, forming an enolate, or the ester molecule may undergo a nucleophilic substitution called transesterification
Sodium_ethoxide
Chemical compound
intramolecular electron transfer to form [{Mn3}–enolate]• radical intermediates (e.g., [{Mn3}–enolate]), instead of free •CH2CO2H radical intermediates
Manganese(III)_acetate
Type of strain energy in organic chemistry
of the reaction. The Z enolate was created to avoid the allylic strain with oxazolidinone. The formation of a specific enolate enforces the development
Allylic_strain
Chemical compound
reactant. It is created from acetyl-CoA, a thioester, which reacts with the enolate of a second molecule of acetyl-CoA in a Claisen condensation reaction,
Acetoacetyl-CoA
Chemical reaction
an enolate. The enolate is the very stable conjugate base of the starting material, and is one of the intermediates in the reaction. This enolate then
E1cB-elimination_reaction
Molecules which are non-mirror image, non-identical stereoisomers
Note also the example of the stereochemistry of ketonization of enols and enolates. Cahn–Ingold–Prelog priority rules for nomenclature. IUPAC "Gold Book"
Diastereomer
Chemical reaction
Willard, A. K. (1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". J. Am. Chem. Soc. 98
Ireland–Claisen_rearrangement
Chemical reaction
doi:10.1016/S0040-4039(00)77444-2 Asymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate Erin C. Burger and Jon A. Tunge Org. Lett
Carroll_rearrangement
Chemical reaction
forming an enolate. A proton transfer occurs, forming another enolate via deprotonation of the carbon atom attached to the R group. Using the enolate, an aldol
Fujimoto–Belleau_reaction
Locally acting nonsteroidal anti-inflammatory drug
which undergoes spontaneous internal hydrazide formation. Treatment of the enolate of this amide with 3-chloro-1-dimethylamino propane gives benzydamine (5)
Benzydamine
Concept in organic chemistry
defined: enolendo and enolexo, which refer to whether both carbons of the enolate C-C fragment are (respectively) incorporated into the ring formed or not
Baldwin's_rules
Colorless gas with the formula NO
reaction is the addition of a two equivalents of nitric oxide onto an enolate, giving a diazeniumdiolate (also called a nitrosohydroxylamine). The product
Nitric_oxide
Functional group of organic compounds
N-tert-butyl benzenesulfinimidoyl chloride[citation needed] or IBX oxidize an enolate, the result is 1,4-elimination. Finally, the Meyer–Schuster rearrangement
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
charge over two unlike atoms or over two like but non-equivalent atoms. Enolate ions are Ambident Nucleophile. Wiktionary definition "Merriam- Webster
Ambident_(chemistry)
Organic reaction between a silyl enol ether and an aldehyde or formate
crossed aldol reactions with lithiated imines. Competing work with lithium enolate aldol reactions was published also in 1973 by Herbert O. House. Mukaiyama
Mukaiyama_aldol_addition
aldol reaction, e.g., addition of ketone-derived nucleophiles (enols, enolates), to electrophilic aldehydes that have attached groups varying in size
Flippin–Lodge_angle
Chemical compound
Grignard reagents, organozinc compounds, organolithium compounds, and enolates. Chiral sulfinimines as intermediates for the asymmetric synthesis of amines
Tert-Butanesulfinamide
Transmission of electronic effects through a system of conjugated chemical bonds
electrophile is attacked by a nucleophilic vinylogous enolate (see first and following image). The vinylogous enolate reacts at the terminal position of the double
Vinylogy
Chemical synthesis strategy
this process is reversed when hydrochloric acid is introduced (red). The enolate reacts as an electrophile in a Friedel-Crafts reaction with ring-closure
One-pot_synthesis
Enzyme that regulates the metabolism of fatty acids
decomposes to CO2 and PO3−4. The PO3−4 deprotonates biotin, creating an enolate, stabilized by Arg338, that subsequently attacks CO2 resulting in the production
Acetyl-CoA_carboxylase
Organosulfur chemical compound used as a solvent
sodium. It is a base, e.g., for the deprotonation of ketones to form sodium enolates, phosphonium salts to form Wittig reagents, and formamidinium salts to
Dimethyl_sulfoxide
Class of enzymes
phosphate group to ADP, producing ATP and the enolate of pyruvate. Secondly, a proton must be added to the enolate of pyruvate to produce the functional form
Pyruvate_kinase
Chemical reaction
that may be used as nucleophiles for this process include carbanions and enolates. Alpha hydroxy acids can be converted into amino acids directly using aqueous
Amination
Chemical reaction of diesters
larger rings. Deprotonation of an ester at the α-position generates an enolate ion which then undergoes a 5-exo-trig nucleophilic attack to give a cyclic
Dieckmann_condensation
Molecule containing two adjacent C=O groups
2-substituted derivatives are known. They are often prepared by alkylation of the enolate of malondialdehyde. 1,3-Diketones are also called β-diketones. An important
Dicarbonyl
Chemical reaction
description the RC reaction is any coupling of one active alkene / latent enolate to a second Michael acceptor, creating a new C–C bond between the alpha-position
Rauhut–Currier_reaction
Chemical process in which a methyl (CH3) group is covalently attached to a molecule
salt RO− may be likewise methylated to give an ether, ROCH3; or a ketone enolate may be methylated on carbon to produce a new ketone. The Purdie methylation
Methylation
Transition metal carbene complex
carbonyl complex with organolithium compounds. The corresponding lithium enolate-like structure is highly stabilized, and thus, needs to be quenched by
Fischer_carbene
Chemical compound
compounds, and any overtly acidic compounds, to produce alkoxides, amides, enolates and other salts of lithium, respectively. The stability and volatility
N-Butyllithium
Chemical coupling reaction
β-unsaturated ester), just as the Wittig reaction does. To obtain the (Z)-enolate, the Still-Gennari modification of the Horner-Wadsworth-Emmons reaction
Wittig_reaction
Class of organic compounds
the Janovski adduct is oxidized with excess base to a strongly colored enolate with subsequent reduction of the dinitro compound to the aromatic nitro
Meisenheimer_complex
ENOLATE
ENOLATE
ENOLATE
ENOLATE
Boy/Male
Indian, Telugu
A Beautiful Cloud in the Sky
Surname or Lastname
English (Hampshire)
English (Hampshire) : probably an affectionate nickname for someone who lived in the woods.
Male
Native American
Native American Algonquin name NOSH means "father."
Boy/Male
Hindu, Indian
Mind; Cleaver; King; Sharp Mind
Girl/Female
Indian
Brightness
Boy/Male
Gujarati, Hindu, Indian, Kannada, Marathi, Sanskrit, Sindhi, Telugu
Beautiful
Girl/Female
Arabic, Muslim
Favored; Preferred
Boy/Male
Muslim/Islamic
Two garments
Boy/Male
Arabic, Muslim
The Obliterator of Infidelity
Girl/Female
Hindu
Request, Desire
ENOLATE
ENOLATE
ENOLATE
ENOLATE
ENOLATE