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Enolates reactions with

Fluoroalkyl ketones may be used as the electrophilic partners in condensation reactions with other carbonyl compounds The highly electrophilic hexafluo-roacetone has been used in selective hexafluoroisopropyhdenation reactions with enol silyl ethers and dienolsilyl ethers [f] (equation 1)... [Pg.615]

Intermolecular [4C+2S] cycloaddition reactions where the diene moiety is contained in the carbene complex are less frequent than the [4S+2C] cycloadditions summarised in the previous section. However, 2-butadienylcarbene complexes, generated by a [2+2]/cyclobutene ring opening sequence, undergo Diels-Alder reactions with typical dienophiles [34,35] (Scheme 59). Also, Wulff et al. have described the application of pyranylidene complexes, obtained by a [3+3] cycloaddition reaction (see Sect. 2.8.1), in the inverse-electron-demand Diels-Alder reaction with enol ethers and enamines [87a]. Later, this strategy was applied to the synthesis of steroid-like ring skeletons [87b] (Scheme 59). [Pg.99]

Additions of aryl- or alkyllithium reagents to N-silylated formamides 508 give the imines 509 in 55-80% yield [90, 91] some of these imines can subsequently be converted into the corresponding //-lactams by reaction with enolates of alkyl butyrates [92]. Conversion of N-silylated butyrolactam 388 into cyclic Schiff bases such as 390, by reaction with methyl- or butyllithium, via O-silylated butyrolactam 389, is discussed in Section 4.8 (Scheme 5.28). [Pg.97]

Some sugar residues in bacterial polysaccharides are etherified with lactic acid. The biosynthesis of these involves C)-alkylation, by reaction with enol-pyruvate phosphate, to an enol ether (34) of pyruvic acid, followed by reduction to the (R) or (5) form of the lactic acid ether (35). The enol ether may also react in a different manner, giving a cyclic acetal (36) of pyruvic acid. [Pg.303]

Whereas metal-catalyzed decomposition of simple diazoketones in the presence of ketene acetals yields dihydrofurans 121,124,134), cyclopropanes usually result from reaction with enol ethers, enol acetates and silyl enol ethers, just as with unactivated alkenes 13). l-Acyl-2-alkoxycyclopropanes were thus obtained by copper-catalyzed reactions between diazoacetone and enol ethers 79 105,135), enol acetates 79,135 and... [Pg.121]

Besides aldehydes and ketones, TiCl4 activates acetals effectively for reaction with enolates (Scheme 18).70,71 The reactivity of acetals is higher than that of the corresponding aldehydes in... [Pg.406]

In reactions with azides, ketones are directly converted to 5-hydroxytriazolines. Ketone enolate 247, generated by treatment of norbornanone 246 with LDA at 0°C, adds readily to azides to provide hydroxytriazolines 248 in 67-93% yield. Interestingly, l-azido-3-iodopropane subjected to the reaction with enolate 247 gives tetracyclic triazoline derivative 251 in 94% yield. The reaction starts from an electrophilic attack of the azide on the ketone a-carbon atom. The following nucleophilic attack on the carbonyl group in intermediate 249 results in triazoline 250. The process is completed by nucleophilic substitution of the iodine atom to form the tetrahydrooxazine ring of product 251 (Scheme 35) <2004JOC1720>. [Pg.35]

Heterocycles.—The phosphonium salt (59) is an effective three-carbon synthon, as demonstrated by its reaction with enolates of /9-keto-esters (Scheme 20) to give cyclopentenyl sulphides via an intramolecular Wittig reaction.63 Ylides are also intermediates in the synthesis of dihydrofurans (60) from the cyclopropylphos-phonium salt (61) and sodium carboxylates (Scheme 21).64 Cumulated ylides are very useful for the synthesis of heterocyclic compounds, e.g. (62), from molecules which contain both an acidic Y—H bond and a carbonyl or nitroso-function, as shown in Scheme 22.65... [Pg.190]

Acetals of benzaldehydes may undergo EGA-catalyzed aldol reactions also with alkyl enol ethers, (22) (R = alkyl), as nucleophiles [31] but in contrast to the reaction with enol silyl ethers the threo isomer is favored in this case. [Pg.461]

Triethyl orthoformate is often used in reactions with enolates and carbanions to form diethyl acetals that on treatment with dilute acid give the corresponding formyl derivatives. However, when indole is heated at 160 C with triethyl orthoformate the locus of reaction is at N-1 rather than at C-3, and 1-(diethoxymethyl)indole is formed (Scheme 7.6). The A -substituent is easily removed by acidic hydrolysis to reform indole. [Pg.101]

Furthermore, it was recently shown, that enantiopure diaryl methanols can undergo stereospecific SN2-type substitution reactions with enolates at the (di)benzylic carbon affording 1,1-diarylalkyl derivatives (31 — 32 —> 33 Scheme 2.1.2.4). This discovery widened the preparative applicability of diaryl methanols significantly, and was used by Merck in the synthesis of selective PDE-IV inhibitors 34 and 35 [32]. [Pg.180]

Monocyanohydrins of P-diketones.3 In the presence of TiCl4, acetyl cyanide reacts with enol silyl ethers of ketones at - 78° to afford monocyanohydrins of diketoncs in excellent yield. The corresponding reaction with enol silyl ethers aldehydes proceeds in only about 35% yield. A low temperature is essential for this reaction. A similar reaction is possible with allyltrimethylsilane. [Pg.1]

In a remarkable cycloaddition, 1,2-oxazines have been prepared from polystyrene-bound acrylates by reaction with enol ethers and nitroalkenes under high-pressure (Entry 4, Table 15.34). [Pg.452]


See other pages where Enolates reactions with is mentioned: [Pg.816]    [Pg.155]    [Pg.1289]    [Pg.119]    [Pg.121]    [Pg.407]    [Pg.189]    [Pg.1085]    [Pg.772]    [Pg.141]    [Pg.155]   
See also in sourсe #XX -- [ Pg.95 , Pg.227 ]




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1- Butene, 4-nitroaddition reaction with enolates

2-Butanone, 3,3-dimethyllithium enolate reaction with zirconocene/isoprene complex

3- Methyl-5-nitropyrimidin-4- -one reaction with enolate anions

A Tnmethylsilyl enolates reaction with tnfluoromethyl

Acetals reaction with silyl enol ethers

Acid chlorides, reaction with ester enolates

Acid chlorides, reaction with malonate enolates

Acrylic acid, a- methyl ester addition reaction with enolates

Acrylonitrile, 2- addition reactions with enolates

Acyl imidazoles, reaction with ester enolates

Alcohols reaction with enol esters

Alcohols reaction with enol ethers

Aldehydes aldol reactions with silyl enol ethers

Aldehydes enolate anions, reaction with

Aldehydes reaction with silyl enol ethers

Aldehydes reactions with enolates

Aldehydes, a-methyl reaction with enol silanes

Aldehydes, p-alkoxy reaction with enol silanes

Aldehydes, reaction with amide enolate anions

Aldehydes, reaction with anhydride enolates

Aldehydes, reaction with borane enolates

Aldehydes, reaction with ester enolates

Aldehydes, reaction with nitro enolates

Aldol Reaction with () and (Z) Enolates

Aldol condensation aldehyde reaction with enolates

Aldol condensation ketone reaction with enolates

Aldol reactions With boron enolates

Aldol reactions With silyl enol ethers

Aldol reactions With titanium enolates

Aldol-Type Reaction with Silyl Enolates

Allenyl enolates reactions with electrophiles

Amide enolates, reactions with electrophiles

Amides, enolates, reaction with

Aminals reaction with enol silanes

Amino esters, enolates, reaction with

Amino esters, enolates, reaction with halides

Ammonium fluoride, tetrabutylcatalyst enol silane reaction with aldehydes

Anhydrides, reaction with amide enolates

Anhydrides, reaction with enolate anions

Aziridines, reaction with acid enolates

Benzaldehyde, reaction with trimethylsilyl enol ethers

Benzene, iodosylalkane oxidation reaction with silyl enol ethers

Benzenes reaction with lithium enolates

Boron enolates reactions with aldehydes

Bromine reaction with enolates

Bromine reaction with enols

Carbonyl compounds reaction with enol silanes

Chlorides, acyl reaction with ester enolates

Chlorotrimethylsilane reaction with enolate anions

Chlorotrimethylsilane, reaction with ester enolates

Chromyl chloride reaction with silyl enol ethers

Claisen condensation ketone enolate reaction with esters

Conjugated compounds, reaction with enolate anions

Cumulative Subject reactions with enol silanes

Cyanides, a-alkoxyacyl reaction with silyl enol ethers

Cyanides, p-alkoxyacyl reaction with silyl enol ethers

Cyclohexanone, 2,2-dimethyllithium enolate reaction with benzaldehyde

Diastereoselectivity aldehydes, reaction with enolates

Dicarbonyl enolates, reactions with

Dicarbonyl enolates, reactions with electrophiles

Dimethyl disulfide, reaction with lithium enolate

Dioxiranes reaction with enol ethers

Disulfides reaction with enolate anions

Electrophiles reactions with enolates

Enol acetates reaction with methyllithium

Enol acetates, reaction with

Enol acetates, reaction with organolithium reactions

Enol esters reaction with carbonyl compounds

Enol esters reaction with carboxylic acids

Enol ether reaction with azetidinone

Enol ethers reaction with acetals

Enol ethers reaction with benzeneselenenyl chloride

Enol ethers reaction with carbonyl compounds

Enol ethers reactions with electrophilic carbon

Enol ethers reactions with singlet oxygen

Enol phosphates reaction with dialkylcuprates

Enol reaction with ethyl

Enol silanes reaction with acetals

Enol silanes reaction with aldehydes

Enol silanes reaction with aldehydes, diastereoselectivity

Enol silanes reaction with aldehydes, stereoselectivity

Enol silanes reaction with chiral a-alkoxy aldehydes

Enol silanes reaction with chiral a-methyl aldehydes

Enol silanes reaction with chiral acetals

Enol silanes reaction with chiral azetinones

Enol silanes reaction with dimethyl acetals

Enol silanes reaction with imines

Enol silanes, nonstereogenic reaction with aldehydes

Enol silanes, nonstereogenic reaction with aldehydes, diastereoselectivity

Enol silanes, stereogenic reaction with aldehydes

Enol silanes, stereogenic reaction with chiral azetinones

Enol silyl ethers, reaction with acetals/ketals

Enol sulfonates reaction with acetals

Enol sulfonates reaction with carbonyl compounds

Enolate Reactions with Carbonyl Groups

Enolate Reactions with Non-Carbonyl Electrophiles

Enolate anions reaction with acyl halides

Enolate anions reaction with alkyl halides

Enolate anions reaction with esters

Enolate anions, addition reactions nucleophilic displacements with

Enolate anions, amide, reaction with

Enolate anions, amino-esters, reaction with

Enolate anions, chloro-esters, reaction with

Enolate anions, cyano esters, reaction with

Enolate anions, dianions reaction with alkyl halides

Enolate anions, dianions, reaction with

Enolate anions, ester reaction with acid chlorides

Enolate anions, esters, reaction with aldehydes

Enolate anions, esters, reaction with alkyl halides

Enolate anions, esters, reaction with imines

Enolate anions, esters, reaction with nitriles

Enolate anions, lactams, reaction with

Enolate anions, lactones, reaction with

Enolate anions, malonate, reaction with

Enolate anions, malonate, reaction with halides

Enolate anions, malonate, reaction with ketones

Enolate anions, malonic acid, reaction with

Enolate anions, malonic acid, reaction with aldehydes

Enolate anions, nitro compounds, reaction with

Enolate anions, nitro compounds, reaction with aldehydes

Enolate anions, reaction with allylic esters

Enolate reaction with aldehydes

Enolates aldol reaction with

Enolates continued) reaction with aldehydes

Enolates ester enolate reaction with esters (Claisen

Enolates ketone enolate reaction with esters

Enolates reaction with alkyl halide

Enolates reaction with aziridines

Enolates reaction with carbonyl compounds

Enolates reaction with epoxides

Enolates reaction with trialkylboranes

Enolates reaction, with acyl chlorides

Enolates reactions with arynes

Enolates, boron reactions with imines

Enolates, silyl reactions with electrophiles

Enols and reactions with

Enols reactions with

Enols reactions with

Enols reactions with a-selenoalkyl metals

Enones reaction with zinc ester enolates

Epoxides, reaction with amide enolates

Ester enolates reaction with

Ester enolates reaction with compounds

Ester enolates reactions with electrophiles

Esters reaction with ketone enolate anions

Esters, conjugated, reaction with nitrile enolates

Esters, reaction with amide enolates

Ethane, nitroaddition reaction with enolates

Ethers, enol reaction with carbenes

Ethers, enol reaction with dioxirane

Ethers, enol silyl, reaction with iminium salts

Ethers, enol, addition Mannich reaction with

Ethers, silyl enol reaction with organolithium

Fluorides enol silane reaction with aldehydes

Glycinal, reaction with ester enolates

Grignard reagents, reaction with enol-ketones

Halides silyl, reaction with enolate

Halides, alkyl reaction with ketone enolate anions

Halides, alkyl, reaction with amino ester enolates

Halides, alkyl, reaction with ester enolates

Halides, alkyl, reaction with lactone enolates

Halides, alkyl, reaction with malonate enolates

Halides, alkyl, reaction with nitrile enolates

Halides, aryl reaction with enolate anions

Hard electrophiles reaction with enolate

Imines reactions with enolates

Imines, reaction with ester enolates

Imines, reaction with malonic acid enolates

Imines, reactions with silyl enol ethers

Imines, reactions with silyl enolates

Iminium ions reaction with enol silanes

Isoquinoline, 3,4-dihydroreaction with phthalide enolates Mannich reaction

Ketenes addition reaction with enolates

Ketenimines reactions with enolates

Ketone enolates, reactions with aryne

Ketone enolates, reactions with electrophiles

Ketones reaction with enol esters

Ketones reaction with ester enolates

Ketones, a- vinyl reaction with enolates

Ketones, enol, reaction with

Ketones, reaction with boron enolates

Ketones, reaction with enolate anions

Ketones, reaction with malonate enolates

Ketones, reaction with nitro enolates

Ketones, reaction with silyl enol ethers

Ketones, reaction with succinic enolates

Lactams, enolates, reaction with

Lactams, enolates, reaction with halides

Lactones, allylic addition reaction with enolates

Leucarins reaction with enol silyl ether

Lithium enolate reaction with benzaldehyde

Magnesium ester enolates reactions with nitriles

Malonate, enolates, reaction with

Malonate, enolates, reaction with halides

Malonate, enolates, reaction with palladium, acetates

Malonic acid, enolate, reaction with

Malonic acid, enolate, reaction with aldehydes

Mannich bases, preparation reaction with enolates

Mannich reactions with enol

Mannich reactions with enol ethers

Metal enolates reactions with alkenes

Methyllithium reaction with silyl enol ethers

Montmorillonite clays enol ether, reaction with acetals

Nitriles, reaction with ester enolates

Nitrones reaction with enol silanes

Organolithium reagents, reaction with enol acetates

Oxime ethers reactions with enolates

Oxonium ions reaction with enol silanes

Oxygen reaction with enolates

Palladium, organo- compounds reaction with enolates

Peroxides, hexamethyldisilyl reaction with enol acetates

Peroxy acids reaction with enol acetate

Phosphonates addition reaction with enolates

Phthalide enolates reaction with 3,4-dihydroisoquinolines

Phthalide enolates reaction with Schiff bases

Pyridazine reaction with enolates

REACTIONS OF ENOLATE ANIONS WITH ELECTROPHILES

Reaction of enolates with iminium ions or imines

Reaction of stabilized carbanions (enolates) with alkyl halides (enolate alkylation)

Reaction with enol esters

Reaction with enol silyl ethers

Reaction with enolate anions

Reaction with enols or enolates as intermediates

Reaction with fluoro enol

Reaction with fluoro enol phosphates

Reaction with metal enolates

Reaction with nitrile enolate anions

Reaction with palladium compounds Enolization

Reaction with palladium compounds Enols

Reactions of Chiral Ammonium Ketene Enolates as Nucleophiles with Different Electrophiles

Reactions of Enols and Enolates with Electrophiles

Reactions of enolates with aldehydes and ketones the aldol reaction

Reactions of imines with silyl enolates

Reactions with Enolates and Their Derivatives

Reactions with boron enolates

Reactions, with enol ethers

Schiff bases, reaction with ester enolates

Secondary amines addition reactions with enolates

Selenenyl halides reactions with enolates

Silyl enol ether reaction with unsaturated ketone

Silyl enol ethers reaction with nitro olefins

Silyl enol ethers reactions with carbocations

Silyl enol ethers reactions with carbonyl compounds

Silyl enol ethers, reactions with dienes

Soft Electrophiles reaction with enolate

Stereochemistry reaction with enolates

Subject reactions with enol silanes

Sulfenimines reactions with enolates

Sulfones, vinyl addition reaction with enolates

Sulfoxides, vinyl addition reaction with enolates

Tetracyanoethylene reaction with enol ethers

Thioamide enolates, reactions with

Tin, sulfidobis reaction with a-mercurated ketones preparation of enol stannyl ethers

Tosyl, reaction with enolate anions

Trimethylsilyl enol ethers, reaction with

Zinc ester enolates reaction with conjugated enones

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