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Chemical reaction
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new
Aldol_reaction
Type of chemical reaction
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde
Aldol_condensation
Reaction in organic chemistry
and Barbas-List reactions in organic chemistry are a family of proline-catalysed asymmetric aldol reactions. In the 1970s, two research groups
Proline-catalyzed aldol reactions
Proline-catalyzed_aldol_reactions
Organic reaction between a silyl enol ether and an aldehyde or formate
In organic chemistry, the Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether (R2C=CR−O−Si(CH3)3) and
Mukaiyama_aldol_addition
Michael/aldol reaction (or domino Michael/aldol reaction) is a consecutive series of reactions composed of either Michael addition reactions or aldol reactions
Multiple Michael/aldol reaction
Multiple_Michael/aldol_reaction
Modified aldol tandem reaction is a sequential chemical transformation that combines aldol reaction with other chemical reactions that generate enolates
Modified aldol tandem reaction
Modified_aldol_tandem_reaction
The Aldol–Tishchenko reaction is a tandem reaction involving an aldol reaction and a Tishchenko reaction. In organic synthesis, it is a method to convert
Aldol–Tishchenko_reaction
Chemical reaction
type of reaction is also referred to as a nitroaldol reaction (nitroalkane, aldehyde, and alcohol). It is nearly analogous to the aldol reaction that had
Henry_reaction
Organic compound of the form R–CH(OH)–CHR–C(=O)–R
bond-formation reaction, giving them wide applicability as a precursor for a variety of other compounds. Aldols are usually synthesized from an aldol addition
Aldol
Japanese chemist (1927–2018)
the Mitsunobu reaction. The aldol reaction is an essential tool for synthetic chemists. At its simplest, the aldol reaction involves two carbonyl compounds
Teruaki_Mukaiyama
Organic anion formed by deprotonating a carbonyl (>C=O) compound
of Lewis acids (the Mukaiyama aldol reaction): Other important electrophiles are aldehydes/ketones (the aldol reaction) and Michael acceptors. Enamine
Enolate
Type of strain energy in organic chemistry
oxazolidinone. There is another aspect of aldol reaction that is influenced by the allylic strain. On the second aldol reaction, the product which is a 1,3 dicarbonyl
Allylic_strain
Chemical reaction in organic chemistry
transformations termed Tandem Michael-aldol reactions, that sequentially combine Michael addition and aldol reaction into a single reaction. As is the case with Robinson
Robinson_annulation
Chemical reaction involving the formation of sugars from formaldehyde
The reaction is catalyzed by a base and a divalent metal such as calcium. The intermediary steps taking place are aldol reactions, reverse aldol reactions
Formose_reaction
Type of aldol condensation reaction
organic reaction in which a chemical compound containing a carbonyl group (C=O) acts both as the electrophile and the nucleophile in an aldol condensation
Self-condensation
Class of organic chemistry reactions
development of related reactions including the Michael addition, asymmetric aldol reaction, and the Mannich reaction. This reaction has likewise been used
Proline_organocatalysis
Organic reaction
chiral ligands can cause asymmetric Reformatsky additions. Aldol reaction Blaise reaction Claisen condensation Organozinc chemistry Example use in total
Reformatsky_reaction
Protein family
often just aldolase, is an enzyme catalyzing a reversible reaction that splits the aldol, fructose 1,6-bisphosphate, into the triose phosphates dihydroxyacetone
Fructose-bisphosphate aldolase
Fructose-bisphosphate_aldolase
Functional group of organic compounds
Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction. α,β-Unsaturated carbonyl compounds can be subclassified
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
Charged chemical group of the form >CO–
and enantioselective acetate aldol addition reactions. The oxocarbenium ion is used as an electrophile in the reaction. When the methyl group increases
Oxocarbenium
Russian Romantic composer, physician, and chemist (1833–1887)
nucleophilic substitution, as well as being the co-discoverer of the aldol reaction. Borodin was a promoter of education in Russia and founded the School
Alexander_Borodin
Chemical compound
asymmetric synthesis for example in the formation of boron enolates in the aldol reaction. Organic Syntheses, Coll. Vol. 8, p.339 (1993); Vol. 68, p.83 (1990)
Dibutylboron trifluoromethanesulfonate
Dibutylboron_trifluoromethanesulfonate
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
stereoselective transformations, including aldol reactions, alkylation reactions, and Diels-Alder reactions. The oxazolidinones are substituted at the
Chiral_auxiliary
Chemistry
aldol reaction in tandem with dynamic kinetic resolution to obtain a high enantioselective reaction. In this reaction proline catalyzes the reaction through
Dynamic kinetic resolution in asymmetric synthesis
Dynamic_kinetic_resolution_in_asymmetric_synthesis
French chemist (1817–1884)
Wurtz reaction, to form carbon-carbon bonds by reacting alkyl halides with sodium, and for his discoveries of ethylamine, ethylene glycol, and the aldol reaction
Charles_Adolphe_Wurtz
Chemical reaction
with a C=C bond) and the resulting cyclobutane ring undergoes a retro-aldol reaction to yield a 1,5-diketone: The net effect is to add the two carbon atoms
DeMayo_reaction
Chemical reaction
proton acceptor. Typical reactions catalyzed by proton transfer are esterifications and aldol reactions. In these reactions, the conjugate acid of the
Acid_catalysis
Chemical ring forming reaction
bond. These two steps are similar to a base-catalyzed aldol reaction. The oxygen anion in this aldol-like product then SN2 attacks on the formerly-nucleophilic
Darzens_reaction
Chemical reaction
followed by the elimination of water in an E1cB dehydration reaction. Aldol reactions are a key reaction in organic chemistry because they provide a means of
E1cB-elimination_reaction
Index of chemical compounds with the same name
synthesis inhibitor antibiotics and the Evans chiral auxiliaries for aldol reactions. Cycloserine is an antibiotic based on the 3-isoxazolidone parent.
Oxazolidinone
Structural analog of a ketone with selenium replacing oxygen
oxazolidineselones can be used for stereoselective control of aldol reactions, analogous to the Evans aldol reaction that uses oxazolidinones, which allows 77Se-NMR
Selone
Transmission of electronic effects through a system of conjugated chemical bonds
the carbonyl of the methyl ketone. In a vinylogous variation of the aldol reaction, an electrophile is attacked by a nucleophilic vinylogous enolate (see
Vinylogy
Type of Lewis acid catalyst
acid (BLA) catalyzes a number of diene-aldehyde cycloaddition reactions. In the aldol reaction, the diastereoselectivity of the product is often dictated
Chiral_Lewis_acid
American organic chemist (1941–2022)
active molecules. Among his best-known works is the development of aldol reaction methodology (for example, Evans' acyl oxazolidinone method). Evans was
David_A._Evans
Chemical reaction where molecules are combined and a small molecule is lost
biosynthesis of fatty acids. Many variations of condensation reactions exist. Common examples include the aldol condensation and the Knoevenagel condensation, which
Condensation_reaction
Method of synthesizing supramolecular assemblies
reactions. The second type, formation reactions, rely on the formation of new covalent bonds. Some examples include Diels–Alder and aldol reactions.
Dynamic_covalent_chemistry
Reaction sequence in organic chemistry
or aldehyde, a process that may be difficult to achieve directly. The reaction is named after its inventor, Gilbert Stork (Columbia University). The most
Stork_enamine_alkylation
Chemical reactions involving organic compounds
place is much smaller, for example the ene reaction or aldol reaction. Another approach to organic reactions is by type of organic reagent, many of them
Organic_reaction
Use of metal-based Lewis acids to catalyze organic reactions
the aldol reaction, and various pericyclic processes that proceed slowly at room temperature, such as the Diels-Alder reaction and the ene reaction. In
Lewis_acid_catalysis
Chemical compound
a reaction known as the Ehrlich-Sachs reaction: Sometimes condensation with active methylene compounds gives products of O-nitroso-aldol reaction: R–CH2-CHO
Nitrosobenzene
Family of chiral diphosphine ligands used for asymmetric catalysis
Laboratories previously-known ferrocenyl ligands for a Au(I)-catalyzed aldol reaction. Togni's team began considering diphosphine ligands, and technician
Josiphos_ligands
Chemical reaction
prior, the reaction begins with 1,4-addition of the catalytic amine to the activated alkene. The resulting zwitterionic aza-enolate undergoes aldol addition
Baylis–Hillman_reaction
Chemical reaction
carbon-carbon bond forming reactions in organic chemistry, including the aldol reaction, Henry reaction (nitro-aldol reaction) and Mannich reaction. Although extensive
Nitro-Mannich_reaction
components of an aldol reaction are combined with the asymmetric catalyst S-proline in a ball mill in a mechanosynthesis. The reaction product has 97%
Dry_media_reaction
Chemical reaction
typical reactions of aldehydes such as the aldol reaction. Other possible electrophiles include aldehydes, amides, and esters. The reaction between lithiated
Corey–Seebach_reaction
Functional group made of a ketone (>C=O) and hydroxyl (–OH) group on nearby carbons
Fehling's test. Beta-hydroxy ketones are a type of aldol. They are commonly formed by an aldol reaction between two carbonyl compounds. A simple example
Hydroxy_ketone
Triflate salts of the lanthanides
catalysed Michael additions and aldol reactions can be used. For aromatic nitro compounds, synthesis is via a substitution reaction. The standard synthesis is
Lanthanide trifluoromethanesulfonates
Lanthanide_trifluoromethanesulfonates
Chemical compound
produced by cooking or drying of the ginger root, which causes a reverse aldol reaction on gingerol. Zingerone was first isolated from the ginger root in 1917
Zingerone
Study of compounds with carbon to zinc bonds
after protonation. The benefits of the Reformatsky reaction over the conventional aldol reaction protocols is the following: Allows for exceedingly derivatized
Organozinc_chemistry
reaction takes place. An alternative classification with broader scope is suggested by Yujiro Hayashi as he describes certain organocatalytic Aldol reactions
On-water_reaction
Organic chemical reaction
[ˈknøːvənaːɡl̩]) reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A
Knoevenagel_condensation
Organic chemical reaction
deprotonation there, leading to enolates and possible aldol reactions. Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic
Cannizzaro_reaction
Method in organic chemistry
interconnected field. In this reaction, naturally occurring chiral proline is the chiral catalyst in an aldol reaction. The starting material is an achiral
Organocatalysis
the outcome of carbon-carbon bond-forming reactions in solution. An important example is the aldol reaction, e.g., addition of ketone-derived nucleophiles
Flippin–Lodge_angle
Organic reaction developed by William Henry Perkin
β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence
Perkin_reaction
Organic chemistry reaction
Japp–Maitland condensation is an organic reaction and a type of Aldol reaction and a tandem reaction. In a reaction between the ketone 3-pentanone and the
Japp–Maitland_condensation
Chemical compound
(the Gatterman-Koch reaction). Natural benzaldehyde is produced from cinnamaldehyde obtained from cassia oil by the retro-aldol reaction: the cinnamaldehyde
Benzaldehyde
Chemical reaction
Tishchenko reaction discovered in 1906. The Aldol–Tishchenko reaction provides another potential route to 1,3-diol monoester products. The reaction mechanism
Evans–Tishchenko_reaction
Japanese chemist (1927–2022)
Hiroshi; Tsuji, Jiro (May 1989). "The palladium-catalyzed directed aldol reaction of aldehydes with ketone enolates generated by the decarboxylation of
Jirō_Tsuji
Organic compound containing the functional group R–CH=O
additions, Barbier reactions, and the Nozaki–Hiyama–Kishi reaction. In the aldol reaction, the metal enolates of ketones, esters, amides, and carboxylic
Aldehyde
Monosaccharide with four carbon atoms
transaldolase utilizes a Schiff base to perform a reverse aldol reaction and a forward aldol reaction in its mechanism, generating an erythrose 4-phosphate
Tetrose
Compound with carbon to copper bonds
carbocupration/Mukaiyama aldol reaction sequence (as shown in the figure above) carbocupration favors the formation of the Z-aldol. Ethyl copper Yao, B.;
Organocopper_chemistry
Colorless gas with the formula NO
product can undergo a subsequent retro-aldol reaction, giving an overall process similar to the haloform reaction. For example, nitric oxide reacts with
Nitric_oxide
Class of organosilicon compounds of the form R3Si–O–CR=CR2
are used in many reactions resulting in alkylation, e.g., Mukaiyama aldol addition, Michael reactions, and Lewis-acid-catalyzed reactions with SN1-reactive
Silyl_enol_ether
Chemical reaction
prepared by alternative methods (from butyraldehyde by aldol condensation). Instead, the Guerbet reaction is mainly applied to fatty alcohols to afford oily
Guerbet_reaction
Subdiscipline of chemistry, focusing on carbon compounds
enolate, or as an electrophile; the combination of the two is called the aldol reaction. Designing practically useful syntheses always requires conducting the
Organic_chemistry
Chemical compounds containing C–Li bonds
Lithium dialkylamides (LiNR2) are widely used in enolate formation and aldol reaction. The reactivity and selectivity of these bases are also influenced by
Organolithium_reagent
Chemical compound
can be produced. Neopentyl glycol is synthesized industrially by the aldol reaction of formaldehyde and isobutyraldehyde. This creates the intermediate
Neopentyl_glycol
Inorganic salt: MgCl2 and its hydrates
polypropylene. Magnesium chloride is also a Lewis acid catalyst in aldol reactions. Magnesium chloride is used for low-temperature de-icing of highways
Magnesium_chloride
Disproportionation reaction of aldehydes
hydride transfer mechanism between aldehydes. Aldol–Tishchenko reaction Baylis–Hillman reaction Cannizzaro reaction Meerwein–Ponndorf–Verley reduction Oppenauer
Tishchenko_reaction
Most abundant structural protein in animals
tropocollagen molecules form collagen fibrils, via covalent cross-linking (aldol reaction) by lysyl oxidase which links hydroxylysine and lysine residues. Multiple
Collagen
Pericyclic chemical reaction
used masked-aldol reaction. Cycloaddition between a nitrile oxide and an alkene yields the cyclic isoxazoline product, whereas the reaction with an alkyne
1,3-Dipolar_cycloaddition
Chemical compound
Some of the main reactions this compound can induce are nucleophilic addition, aldol reactions, alkylation, hydration and redox reactions. For example, fluoroacteone
Fluoroacetone
Chemical compound
desired bispidine. The reaction conditions need to be controlled to avoid the competitive aldol reaction. Indeed the reaction solution should be as concentrated
Bispidine
Study of compounds containing gold–carbon bonds
reaction constitutes the first example of a catalytic, asymmetric aldol reaction. In contrast to the other reactions described above, this reaction does
Organogold_chemistry
Chemical reaction
natural product synthesis for building complex skeletons. Aldol reaction "Iwanow Reaction". Organic Chemistry Portal. Retrieved 17 June 2025. ^ Ivanov
Ivanov_reaction
Chemical compound
6-secocholestan-6-al. Atheronal B (secosterol B) is formed by the intramolecular aldol reaction of atheronal A, which is 3β-hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde
Atheronals
Chemical group (–OSO2CF3) or anion (charge –1)
triflate is used in such reactions as aldol reactions and Diels–Alder reactions. An example is the Mukaiyama aldol addition reaction between benzaldehyde
Triflate
Reaction in organic chemistry
react efficiently to form a new carbon–carbon bond. Like the aldol addition, the Michael reaction may proceed via an enol, silyl enol ether in the Mukaiyama–Michael
Michael_addition_reaction
Chemical compound
is used as a Lewis acid catalyst in some organic synthesis, e.g., in aldol reaction. Magnesium bromide also has been used as a tranquilizer and as an anticonvulsant
Magnesium_bromide
Chemical reaction(s) which favor one chiral isomer over another
number of carbon–carbon bond forming reactions become enantioselective in the presence of proline with the aldol reaction being a prime example. Organocatalysis
Enantioselective_synthesis
Monoamide of a phosphite diester
Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc Reagents" (PDF). Angewandte Chemie International Edition
Phosphoramidite
Cholesterol-lowering medication
first of the two alcohol functional groups via a diastereoselective aldol reaction. Once the compound entered pre-clinical development, process chemistry
Atorvastatin
Topics referred to by the same term
Mukaiyama may refer to: Mukaiyama aldol addition, an organic reaction Mukaiyama hydration, an organic reaction Mukaiyama Kofun, a kofun burial mound located
Mukaiyama
Class of chiral ligands
observed for aldol-type reactions, Mannich-type reactions, ene reaction, Michael addition, Nazarov cyclization, and hetero-Diels-Alder reaction. On the other
Bisoxazoline_ligand
Chemical reaction
Aldol reaction to 6 and elimination to 7. The Pfitzinger reaction and the Niementowski quinoline synthesis are variations of the Friedländer reaction
Friedländer_synthesis
discovered Borodin reaction, co-discovered Aldol reaction Aleksandr Butlerov, discovered hexamine, formaldehyde and formose reaction (the first synthesis
List_of_Russian_people
Chemical agent and drug construction
amine 8, which upon reaction with 2-iodoxybenzoic acid gave ketone 9, the first major building block of the synthesis. The aldol reaction of ketone 9 with
Quinine_total_synthesis
Chemical compound
African Ginger species. Cooking ginger transforms gingerol via a reverse aldol reaction into zingerone, which is less pungent and has a spicy-sweet aroma. When
Gingerol
Organic chemical compound
synthesis. In addition reactions acetaldehyde is prochiral. It is used primarily as a source of the "CH3C+H(OH)" synthon in aldol reactions and related condensation
Acetaldehyde
Japanese chemist
asymmetric Heck reaction, Tetrahedron 53 (1997) 7371–7395. Gröger H, Vogl EM, Shibasaki M: New catalytic concepts for the asymmetric aldol reaction, Chemistry
Masakatsu_Shibasaki
Class of chemical compounds
other to deliver epothilone B in an approach including Wittig reaction, aldol reaction, and Yamaguchi esterification (Figure 3). Preparative thin-layer
Epothilone
Oxidisation reaction
flavor. The aldehyde is comparatively reactive and readily participates in aldol condensations. Benzaldehyde can serve as a precursor for various compounds
Étard_reaction
author of the famous opera Prince Igor, discovered Borodin reaction, co-discovered Aldol reaction Alexander Chizhevsky, interdisciplinary scientist, biophysicist
List_of_Russian_scientists
Covalent bond between two carbon atoms
bonds are the aldol reaction, Diels–Alder reaction, Grignard reaction, cross-coupling reactions, the Michael reaction and the Wittig reaction. The directed
Carbon–carbon_bond
Chemical compound
pentaerythritol synthesis and in the crossed Cannizzaro reaction of formaldehyde with the aldol reaction product trimethylol acetaldehyde [3-hydroxy-2
Sodium_formate
Chemical compound
organic synthesis. In particular, it catalyzes the Michael reaction and the Mukaiyama aldol reaction. The addition of other metal iodides increases its catalytic
Bismuth_chloride
Chemical compound
NaI + BiI3 → Na2[BiI5] Bismuth(III) iodide catalyzes the Mukaiyama aldol reaction. Bi(III) is also used in a Barbier type allylation of carbonyl compounds
Bismuth(III)_iodide
Chemical compound
precursor as the intermediate, aldol adduct, is a crystalline solid. A chelation-controlled Mukaiyama-aldol reaction was used to set the stereogenicity
Discodermolide
Chemical compound
and being a scaffold for certain chemical reactions. NOBIN is an excellent catalyst for the aldol reaction producing reliable products, good yields, and
NOBIN
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