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searching for Enolate 109 found (219 total)

alternate case: enolate

Conia-ene reaction (1,805 words) [view diff] exact match in snippet view article find links to article

form a metal-stabilized enolate, which then attacks the tethered alkyne and transfers the metal cation. An early example of enolate activation was reported

Lectka enantioselective beta-lactam synthesis (317 words) [view diff] exact match in snippet view article find links to article

carbon of the ketene to promote the formation of β-lactams. Chiral ketene enolate formation via nucleophilic activation by the cinchona alkaloid facilitates

Davis oxidation (639 words) [view diff] exact match in snippet view article find links to article

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

Methyl cyanoformate (187 words) [view diff] exact match in snippet view article find links to article

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

Claisen condensation (627 words) [view diff] exact match in snippet view article find links to article

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

Reformatsky reaction (1,269 words) [view diff] exact match in snippet view article find links to article

'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates or Grignard

Carbonyl α-substitution reactions (982 words) [view diff] exact match in snippet view article find links to article

of an α hydrogen atom by an electrophile, E, through either an enol or enolate ion intermediate. Because their double bonds are electron rich, enols behave

Knoevenagel condensation (691 words) [view diff] exact match in snippet view article find links to article

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

Ireland–Claisen rearrangement (236 words) [view diff] exact match in snippet view article find links to article

Willard, A. K. (1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". J. Am. Chem. Soc. 98

Stepwise reaction (306 words) [view diff] exact match in snippet view article find links to article

steps: Deprotonation next to (α to) the carbonyl: HC−C=O → C=C−O− Attack of enolate: Rδ+ + C=C−O− → R−C−C=O Rδ+ is an electron acceptor, for example, the carbon

Chiral auxiliary (3,692 words) [view diff] exact match in snippet view article find links to article

strong base such as lithium diisopropylamide selectively furnishes the (Z)-enolate, which can undergo stereoselective alkylation. Alkylation of an oxazolidinone

Self-condensation (488 words) [view diff] exact match in snippet view article find links to article

cannot form an enolate, and the benzaldehyde is much more electrophilic than any unenolized acetophenone in solution. Therefore, the enolate formed from

Macrophomic acid (540 words) [view diff] exact match in snippet view article find links to article

decarboxylated to form an enolate that coordinates to a Mg2+ metal center (2) found in the active site of the enzyme. Then, the coordinated enolate can either add

Ketone (2,948 words) [view diff] exact match in snippet view article find links to article

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

2,4 Dienoyl-CoA reductase (1,747 words) [view diff] exact match in snippet view article find links to article

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

Carbonyl oxidation with hypervalent iodine reagents (1,207 words) [view diff] exact match in snippet view article find links to article

carbonyl compounds through the intermediacy of a hypervalent iodine(III) enolate species. This electrophilic intermediate may be attacked by a variety of

Phosphoenolpyruvate carboxylase (1,883 words) [view diff] exact match in snippet view article find links to article

carbon dioxide is attacked by the enolate to form oxaloacetate. The metal cofactor is necessary to coordinate the enolate and carbon dioxide intermediates;

John Isaiah Brauman (679 words) [view diff] exact match in snippet view article find links to article

of (E)- and (Z)-Propionaldehyde Enolate Anions. Electron Affinities of the Stereoisomers of Propionaldehyde Enolate Radicals". 119. J. Am. Chem. Soc

Muconate lactonizing enzyme (2,057 words) [view diff] exact match in snippet view article find links to article

mechanism that MLEs undergo are the reverse of beta-elimination in which the enolate alpha-carbon is protonated. MLEs can undergo mutations caused by a deletion

Steroid Delta-isomerase (3,232 words) [view diff] exact match in snippet view article find links to article

whether it exists as the enolate or enol. Pollack uses a thermodynamic argument to suggest the intermediate exists as the enolate. The general base Asp-38

Citrate synthase (1,155 words) [view diff] exact match in snippet view article find links to article

atom of Asp-375 deprotonating acetyl CoA's alpha carbon atom to form an enolate anion which in turn is neutralized by protonation by His-274 to form an

2,5-Diketopiperazine (2,289 words) [view diff] exact match in snippet view article find links to article

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

Dieckmann condensation (286 words) [view diff] exact match in snippet view article find links to article

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

Baylis–Hillman reaction (2,788 words) [view diff] exact match in snippet view article find links to article

catalytic amine to the activated alkene. The resulting zwitterionic aza-enolate undergoes aldol addition to the aldehyde. Intramolecular proton shift then

Barton–Zard reaction (277 words) [view diff] exact match in snippet view article find links to article

α-isocyanide. Michael-type addition between the α-isocyanide carbonyl enolate and the nitroalkene. 5-endo-dig cyclization (see: Baldwin's rules). Base

Allylic strain (2,466 words) [view diff] exact match in snippet view article find links to article

of the reaction. The Z enolate was created to avoid the allylic strain with oxazolidinone. The formation of a specific enolate enforces the development

1,3-Indandione (294 words) [view diff] exact match in snippet view article find links to article

diketone, As a solution in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density

Non-nucleophilic base (354 words) [view diff] exact match in snippet view article find links to article

lithium diisopropylamide, is used to deprotonate an ester to give the enolate in the Claisen ester condensation, instead of undergoing a nucleophilic

Enamine (1,800 words) [view diff] exact match in snippet view article find links to article

synthetically useful due to their nucleophilicity (they are more nucleophilic than enolates). Thus they are better able to react with weaker electrophiles (for example

Biosynthesis of cocaine (803 words) [view diff] exact match in snippet view article find links to article

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

(2R)-2-Methylpent-4-enoic acid (220 words) [view diff] exact match in snippet view article

and DMAP as an acyl carrier catalyst addition of a pentene group via enolate addition using Sodium bis(trimethylsilyl)amide as a base and allyl iodide

Triethyl phosphite (448 words) [view diff] exact match in snippet view article find links to article

approach can be utilized for carbonyl α-hydroxylation by reacting the enolate with oxygen, producing an α-hydroperoxide which can be reduced by triethyl

Vancosamine (566 words) [view diff] exact match in snippet view article find links to article

next step, EvaA dehydrates molecule 1 by deprotonating at 3-C to form and enolate, which then eliminates 2-OH, to form molecule 2. Molecule 2 is transformed

Synergistic catalysis (1,045 words) [view diff] exact match in snippet view article find links to article

chiral transition metal complexes. In their proposed mechanism schemes, an enolate is formed from an α-cyano ester and coordinates to the rhodium catalyst

Nucleophilic addition (910 words) [view diff] exact match in snippet view article find links to article

amine with formaldehyde and a carbonyl compound in the Mannich reaction an enolate ion in an aldol reaction or Baylis–Hillman reaction an organometallic nucleophile

Rubottom oxidation (3,396 words) [view diff] exact match in snippet view article find links to article

hydride (KH) and 18-crown-6 (18-C-6) to effect the anionic oxy-Cope, the enolate intermediate was trapped with trimethylsilyl chloride (TMSCl). The silyl

Dihydroxyphenylglycine (506 words) [view diff] exact match in snippet view article find links to article

form a C8 intermediate. DpgB/D then dehydrates the intermediate using enolate chemistry to promote the loss of water. DpgB/D isomerizes the product to

Erlenmeyer–Plöchl azlactone and amino-acid synthesis (578 words) [view diff] exact match in snippet view article find links to article

modification), thiohydantoin and rhodanine have each been employed as the enolate-forming component of the condensation. 2,5-Diketopiperazine can be used

Umpolung (1,774 words) [view diff] exact match in snippet view article find links to article

the α,β-unsaturated ester 1 at the β-position forming the intermediate enolate 2. Through tautomerization 2b can displace the terminal bromine atom to

(4+3) cycloaddition (1,268 words) [view diff] exact match in snippet view article

for generating symmetric oxyallyl cations. After formation of a metal enolate, dissociation of halide generates a positively charged oxyallyl intermediate

2,3-Wittig rearrangement (1,449 words) [view diff] exact match in snippet view article find links to article

(1987). "Asymmetric [2,3]-Wittig rearrangement involving a chiral ester enolate terminus. A chiral synthesis of erythro-.ALPHA.-hydroxy-.BETA.-alkyl carboxylic

Haloform reaction (1,179 words) [view diff] exact match in snippet view article find links to article

basic conditions, the ketone undergoes keto-enol tautomerisation. The enolate undergoes electrophilic attack by the hypohalite (containing a halogen

Pyruvate carboxylase (2,678 words) [view diff] exact match in snippet view article find links to article

an as yet unidentified active site residue, to generate an enolate intermediate. The enolate intermediate then attacks CO2 transiently released from the

Alkynylation (1,249 words) [view diff] exact match in snippet view article find links to article

alkynylations on compounds that are liable to polymerization reactions via enolate intermediates. However, substituting lithium for sodium or potassium acetylides

Pimelic acid (386 words) [view diff] exact match in snippet view article find links to article

additional carbon is supplied by dimethyloxalate, which reacts with the enolate. In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic

Oxazole (616 words) [view diff] exact match in snippet view article find links to article

2-formyloxazole. The lithio compound exists in equilibrium with the ring-opened enolate-isonitrile, which can be trapped by silylation. Electrophilic aromatic

Meisenheimer complex (657 words) [view diff] exact match in snippet view article find links to article

the Janovski adduct is oxidized with excess base to a strongly colored enolate with subsequent reduction of the dinitro compound to the aromatic nitro

Biotin carboxylase (1,048 words) [view diff] exact match in snippet view article find links to article

An enolate-like intermediate is formed, producing a negative charge on the oxygen, which is stabilized by the iminium ion of Arg338. The enolate then

W. Clark Still (2,031 words) [view diff] exact match in snippet view article find links to article

at elevated temperature to induce the rearrangement, and the resulting enolate was trapped with chlorotrimethylsilane to form the macrocyclic silyl enol

Aza-Cope rearrangement (5,704 words) [view diff] exact match in snippet view article find links to article

reactions, conversion of the Z-enolate affords lower selectivity due to 1,3 diaxial steric interactions between the enolate and the ring, as well as the

Monocerin (515 words) [view diff] exact match in snippet view article find links to article

methyl transferase is considered to be a tailoring enzyme. Formation of an enolate ion on the carbon three carbons away from sulfur allows aldol addition

Tazarotene (1,179 words) [view diff] exact match in snippet view article find links to article

presence of aluminium chloride gives the methyl ketone (4). Reaction of the enolate of that ketone with diethyl chlorophosphate gives the enol phosphate 5

Wittig reaction (1,600 words) [view diff] exact match in snippet view article find links to article

β-unsaturated ester), just as the Wittig reaction does. To obtain the (Z)-enolate, the Still-Gennari modification of the Horner-Wadsworth-Emmons reaction

Allenes (4,081 words) [view diff] exact match in snippet view article find links to article

Alvin K. (May 1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". Journal of the American

Ionone (815 words) [view diff] exact match in snippet view article find links to article

catalysed. The aldol condensation product 5 eliminates water through the enolate ion 6 to form pseudoionone 7. The reaction proceeds by acid catalysis where

Ylide (1,152 words) [view diff] exact match in snippet view article find links to article

both phosphine and ylide functionalities, and can exist in ylidic and enolate forms. These ligands can therefore be engaged in different kinds of bonding

17α-Methyl-19-norprogesterone (261 words) [view diff] exact match in snippet view article find links to article

JF, Pidacks V, Conrow RB, Coscia CJ (1964). "The formation of steroid enolate anions by reductive procedures". Tetrahedron. 20 (2): 357–372. doi:10

5α-Reductase (4,015 words) [view diff] exact match in snippet view article find links to article

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.

Electrophilic amination (2,074 words) [view diff] exact match in snippet view article find links to article

elimination of sulfinic acid. The most synthetically useful aminations of enolate anions employ N-acyloxazolidinone substrates. The chiral auxiliaries on

Ethyl acetoacetate (506 words) [view diff] exact match in snippet view article find links to article

RCH2C(O)CH(Na)CO2Et + LiX Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example

Malondialdehyde (922 words) [view diff] exact match in snippet view article find links to article

Malondialdehyde is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C). Malondialdehyde results from lipid peroxidation of polyunsaturated

Work-up (787 words) [view diff] exact match in snippet view article find links to article

Pauline; Maulide, Nuno (2017-11-15). "Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides". Journal of the American Chemical Society. 139

Mukaiyama aldol addition (958 words) [view diff] exact match in snippet view article find links to article

crossed aldol reactions with lithiated imines. Competing work with lithium enolate aldol reactions was published also in 1973 by Herbert O. House. Mukaiyama

Sodium acetylacetonate (217 words) [view diff] exact match in snippet view article find links to article

established by X-ray crystallography. The sodium cation is bonded to the enolate oxygen centers. Sahbari, J. J.; Olmstead, M. M. (1983). "Structure of Sodium

Hydrogen-bond catalysis (4,562 words) [view diff] exact match in snippet view article find links to article

aldehydes can be effected with high enantioselectivity. The nucleophile is an enolate-type species generated from the conjugate addition of PEt3 to the enone

Asymmetric nucleophilic epoxidation (1,634 words) [view diff] exact match in snippet view article find links to article

in solution coordinate both the peroxide oxygen and the enolate oxygen. Attack of the enolate on the peroxide oxygen generates the epoxide product and

Menthofuran (433 words) [view diff] exact match in snippet view article find links to article

allenyldimethylsulfonium bromide in two steps via a furannulation strategy consisting of enolate addition and rearrangement. Menthofuran is a metabolite of pulegone. Both

1,3-Cyclohexanedione (284 words) [view diff] exact match in snippet view article find links to article

to 3-alkoxyenones. Its pKa is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which also exists

Menthofuran (433 words) [view diff] exact match in snippet view article find links to article

allenyldimethylsulfonium bromide in two steps via a furannulation strategy consisting of enolate addition and rearrangement. Menthofuran is a metabolite of pulegone. Both

Epothilone (2,163 words) [view diff] exact match in snippet view article find links to article

total synthesis of epothilone A was achieved via an intramolecular ester enolate-aldehyde condensation. Other syntheses of epothilones have been published

Isomerase (3,592 words) [view diff] exact match in snippet view article find links to article

mechanism involves the deprotonation of that third carbon to form a reactive enolate intermediate. The enzyme's active site contains two Asp residues. After

Protecting group (6,755 words) [view diff] exact match in snippet view article find links to article

doi:10.1021/ja00325a032. Steven D. Burke, Gregory J. Pacofsky: "The ester enolate claisen rearrangement. Total synthesis of (±)-ethisolide", in: Tetrahedron

N-Butyllithium (1,856 words) [view diff] exact match in snippet view article find links to article

compounds, and any overtly acidic compounds, to produce alkoxides, amides, enolates and other salts of lithium, respectively. The stability and volatility

Jirō Tsuji (1,032 words) [view diff] exact match in snippet view article find links to article

catalytic Pd(OAc)2 and PPh3 via the intermediacy of an allylpalladium enolate - a catalytic Carroll rearrangement. Following work revealed that replacement

James P. Collman (486 words) [view diff] exact match in snippet view article find links to article

North Carolina at Chapel Hill, Stanford University Thesis The Magnesium Enolate of 2,2-Diphenylcyclohexanone (1958) Doctoral advisor Reynold C. Fuson Doctoral

Acetyl cyanide (406 words) [view diff] exact match in snippet view article find links to article

reactions can occur with acetyl cyanide as a reactant; aldol condensation and enolate substitution. Aldol condensation can occur when acetyl cyanide reacts with

Benzydamine (1,071 words) [view diff] exact match in snippet view article find links to article

which undergoes spontaneous internal hydrazide formation. Treatment of the enolate of this amide with 3-chloro-1-dimethylamino propane gives benzydamine (5)

Methylglyoxal synthase (2,029 words) [view diff] exact match in snippet view article find links to article

catalyzed by either Asp71 or Asp101. Protonation of the methylene group of the enolate is non-stereospecific. The reaction products are released sequentially

1,1-Diiodoethane (382 words) [view diff] exact match in snippet view article find links to article

1-diiodoethane as a reactant. Moreover, is can also be used as a reactant in enolate substitution reaction as the following examples. 1,2-Diiodoethylene 1,2-Difluoroethane

Nitro-Mannich reaction (2,892 words) [view diff] exact match in snippet view article find links to article

Summary of enolate and nitronate nucleophilic additions to imines and aldehydes/ketones.

Avobenzone (2,308 words) [view diff] exact match in snippet view article find links to article

than undoped titanium dioxide to improve avobenzone's stability. As an enolate, avobenzone forms with heavy metal ions (such as Fe3+) colored complexes

Ambident (chemistry) (125 words) [view diff] exact match in snippet view article

charge over two unlike atoms or over two like but non-equivalent atoms. Enolate ions are Ambident Nucleophile. Wiktionary definition "Merriam- Webster

3-dehydroquinate dehydratase (941 words) [view diff] exact match in snippet view article find links to article

shikimate pathway of most bacteria. It catalyzes a trans-dehydration using an enolate intermediate. It is heat stable and has Km values one or two orders of

Fatty-acyl-CoA synthase (1,667 words) [view diff] exact match in snippet view article find links to article

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

Acetyl-CoA C-acetyltransferase (288 words) [view diff] exact match in snippet view article find links to article

reaction mechanism: the importance of Asn316 and His348 for stabilizing the enolate intermediate of the Claisen condensation". Biochemistry. 48 (46): 11011–25

Leaving group (2,532 words) [view diff] exact match in snippet view article find links to article

These reactions include loss of a leaving group in the β position of an enolate as well as the regeneration of a carbonyl group from the tetrahedral intermediate

P4-t-Bu (1,550 words) [view diff] exact match in snippet view article find links to article

Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate", J. Org. Chem., vol. 59, no. 18, pp. 5343–5346, doi:10.1021/jo00097a041

Dichloroacetylene (852 words) [view diff] exact match in snippet view article find links to article

52 (15): 3461–3462. doi:10.1021/jo00391a059. "Dichlorovinylation of an Enolate: 8-Ethynyl-8-Methyl-1,4-Dioxaspiro[4.5]Dec-6-Ene". Organic Syntheses. 64:

Medrogestone (2,191 words) [view diff] exact match in snippet view article find links to article

acetate by means of lithium in liquid ammonia leads initially to the 17 enolate ion; this is alkylated in situ with methyl iodide. The now-familiar steric

Cocaine (17,671 words) [view diff] exact match in snippet view article find links to article

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

Hydrogen auto-transfer (1,574 words) [view diff] exact match in snippet view article find links to article

and coworkers have developed enantioselective borrowing hydrogen-type enolate alkylations. As exemplified by the Krische allylation, dehydrogenation

Macrocyclic stereocontrol (2,664 words) [view diff] exact match in snippet view article find links to article

B and lonomycin A, hydroborations such as in 9-dihydroerythronolide B, enolate alkylations such as in (±)-3-deoxyrosaranolide, dihydroxylations such as

Alpha-methylacyl-CoA racemase (2,219 words) [view diff] exact match in snippet view article find links to article

2-methylacyl-CoA to form a deprotonated intermediate (which is probably the enol or enolate) followed by non-sterespecific reprotonation. Thus either epimer is converted

Benzylic activation and stereocontrol in tricarbonyl(arene)chromium complexes (1,352 words) [view diff] exact match in snippet view article

may be deprotonated without side reactions. Alkylation of the resulting enolate proceeds with complete diastereoselectivity to afford the exo product.

Electron affinity (data page) (4,066 words) [view diff] exact match in snippet view article

"Spectroscopy and dynamics of the dipole-bound state of acetaldehyde enolate", J. Chem. Phys., 81 (11): 4883, Bibcode:1984JChPh..81.4883M, doi:10.1063/1

Trifluoromethylation (4,064 words) [view diff] exact match in snippet view article find links to article

trifluoromethylation an early contribution involved reaction of a metal enolate with a trifluoromethyl chalcogen salt in presence of a chiral boron catalyst

Aluminium hydride (3,120 words) [view diff] exact match in snippet view article find links to article

position). The ketone itself is not reduced as it is "protected" as its enolate. Organohalides are reduced slowly or not at all by aluminium hydride. Therefore

Aluminium hydride (3,120 words) [view diff] exact match in snippet view article find links to article

position). The ketone itself is not reduced as it is "protected" as its enolate. Organohalides are reduced slowly or not at all by aluminium hydride. Therefore

Buchwald–Hartwig amination (3,483 words) [view diff] exact match in snippet view article find links to article

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

Teruaki Mukaiyama (2,170 words) [view diff] exact match in snippet view article find links to article

electron-withdrawing triflate group in place of the sulfur. Boron enolates provide an alternative to metal enolates for performing cross-aldol reactions. As an extension

Cascade reaction (2,825 words) [view diff] exact match in snippet view article find links to article

Subsequent cyclization by the intramolecular Michael addition of the enolate into the triple bond of the system gave species 16, which afforded intermediate

Lycoperdon perlatum (3,864 words) [view diff] exact match in snippet view article find links to article

through an endo selective hydroxylation of the chiral bicyclic lactam enolate with MoOPH". Tetrahedron. 58 (48): 9737–40. doi:10.1016/S0040-4020(02)01254-1

Vitamin B12 total synthesis (7,466 words) [view diff] exact match in snippet view article find links to article

Willard, Alvin K. (1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". Journal of the American

Ptaquiloside (3,225 words) [view diff] exact match in snippet view article find links to article

Methylation of the cyclopentanone under Noyori's condition using the TASF enolate produced a mixture of isomers. The undesired isomer 8a can be equilibriumed

Polymer-based battery (2,959 words) [view diff] exact match in snippet view article find links to article

Stabilization depends on the substituents; vicinal carbonyls are stabilized by enolate formation, aromatic carbonyls are stabilized by delocalization of charge

Alexander Nesmeyanov (4,211 words) [view diff] exact match in snippet view article find links to article

(Nesmeyanov – Borisov rule). Thanks to his research, which showed the enolate structure of ketone derivatives with alkali metals and magnesium, that

Ketimine Mannich reaction (3,407 words) [view diff] exact match in snippet view article find links to article

applied and one enantiomer of the 2H-azirine would react with chiral Cu-enolated complex to help overcome its three neighbouring stereogenic centers and

Ketenyl anion (2,090 words) [view diff] exact match in snippet view article find links to article

"Reaction of trimethylsilylketene with strong base. Evidence for ketene enolate formation". The Journal of Organic Chemistry. 43 (2): 376. doi:10.1021/jo00396a057

John P. Richard (2,240 words) [view diff] exact match in snippet view article find links to article

(December 5, 1992). "Generation and stability of a simple thiol ester enolate in aqueous solution". Journal of the American Chemical Society. 114 (26):