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Ability of an achiral molecule to be made chiral in one step
S or R depends on the priority of the incoming group. The concept of prochirality is necessary for understanding some aspects of enzyme stereospecificity
Prochirality
Topics referred to by the same term
determine if a person is suffering shock si, a chemical descriptor; See prochirality Silicon, symbol Si, a chemical element Disulfur diiodide, empirical formula
Si
British biochemist (1911–96)
and by Wrinch that were widely discussed in the 1940s. The concept of prochirality is necessary for understanding some aspects of enzyme stereospecificity
Alexander_George_Ogston
Chemical compound
are less than 100% pure, typically 95%. Although achiral, glycerol is prochiral with respect to reactions of one of the two primary alcohols. Thus, in
Glycerol
Chemical compound which is reduced and oxidized
transfer it from below. Since the C4 carbon that accepts the hydrogen is prochiral, this can be exploited in enzyme kinetics to give information about the
Nicotinamide adenine dinucleotide
Nicotinamide_adenine_dinucleotide
Molecular change in chemistry
Desymmetrization is a chemical reaction that converts prochiral substrates into chiral products. Desymmetrisations are so pervasive that they are rarely
Desymmetrization
is a subset of asymmetric catalytic oxidations. Epoxidations convert prochiral (and other) alkenes to chiral epoxide derivatives. In asymmetric epoxidation
Asymmetric_epoxidation
Chemical compound
liquid is the methyl ester of pyruvic acid. It has attracted interest as a prochiral precursor to alanine and lactic acid. It is prepared by esterification
Methyl_pyruvate
Chemical compound (CH3CH=CH2)
metal-propylene complexes, which are intermediates in these processes. Propylene is prochiral, meaning that binding of a reagent (such as a metal electrophile) to the
Propylene
Organic compound with a C=C–OH group
position of an enol is substituted (i.e., not a methyl ketone), then it is prochiral, forming a new stereocenter when in keto form. Conversely, enolization
Enol
Class of enzymes
are equivalent except that one is "pro-R" and the other "pro-S" (see Prochirality). At this point, the intermediate is rotated 180°. This rotation is referred
Aconitase
Chemical reaction
Corey–Bakshi–Shibata (CBS) reduction, is a chemical reaction in which a prochiral ketone is enantioselectively reduced to produce the corresponding chiral
Corey–Itsuno_reduction
Chemical reaction between molecular hydrogen and another compound or element
catalysts are also used in asymmetric synthesis by the hydrogenation of prochiral substrates. An early demonstration of this approach was the Rh-catalyzed
Hydrogenation
Organic reaction
Baeyer–Villiger oxidations. The first reported instance of one such oxidation of a prochiral ketone used dioxygen as the oxidant with a copper catalyst. Other catalysts
Baeyer–Villiger_oxidation
Technique of oxidizing various substrates
groups that can be prochiral and readily susceptible to oxidation include certain alkenes and thioethers. Challenging but pervasive prochiral substrates are
Asymmetric catalytic oxidation
Asymmetric_catalytic_oxidation
Chemical reaction
require any transition metals. Asymmetric synthesis is possible from prochiral electrophiles. The product's dense functionalization enables many further
Baylis–Hillman_reaction
Chemical compound
a multifunctional molecule that exhibits diverse reactivity. It is a prochiral dienophile. It is a Michael acceptor. Addition of methylmagnesium chloride
Crotonaldehyde
Organic chemical compound
electrophile in organic synthesis. In addition reactions acetaldehyde is prochiral. It is used primarily as a source of the "CH3C+H(OH)" synthon in aldol
Acetaldehyde
Chemical compound
probe of the stereochemistry of reactions involving alkenes because it is prochiral and the two sp2-carbon atoms differ. The regioselectivity and stereoselectivity
1-Methylcyclohexene
Chemical compound
over a copper chromite catalyst: C6H5C(O)CH3 + H2 → C6H5CH(OH)CH3 Being prochiral, acetophenone is also a popular test substrate for asymmetric hydrogenation
Acetophenone
Chemical compound
aldol condensations, oxidations, etc. It is the simplest aldehyde with a prochiral methylene such that α-functionalized derivatives (CH3CH(X)CHO) are chiral
Propionaldehyde
Organic compounds with a carbon-carbon-oxygen ring
coarctate transition state. Chiral epoxides are produced by epoxidation of prochiral alkenes. When the catalyst is chiral or the alkene is chiral, then asymmetric
Epoxide
Reduction method involving hydrazine
used to establish sp3-stereocenters from allylic diazenes containing prochiral stereocenters. The influence of the alkoxy stereocenter results in diastereoselective
Wolff–Kishner_reduction
Organometallic coupling reaction
below. Consequently, when the Grignard reagent adds to an aldehyde or a prochiral ketone, the Felkin-Anh model or Cram's Rule can usually predict which
Grignard_reaction
Naming convention for stereoisomers of molecules
will give the (R)-enantiomer. However, adding a chemical group to the prochiral center from the Re-face will not always lead to an (S)-stereocenter, as
Cahn–Ingold–Prelog priority rules
Cahn–Ingold–Prelog_priority_rules
Class of enzymes which cleave fats via hydrolysis
which means that they can be used for the enantioselective hydrolysis prochiral diesters. Several procedures have been reported for applications in the
Lipase
Chemical group (–CH2–C6H5)
Greg; Simpkins, Nigel S. (1990-01-01). "Asymmetric deprotonation of prochiral ketones using chiral lithium amide bases". Tetrahedron. 46 (2): 523–544
Benzyl_group
Chemical compound
the preparation of certain cyclopropanes in the Kulinkovich reaction. Prochiral thioethers are oxidized enantioselectively using a catalyst derived from
Titanium_isopropoxide
Organic compound or functional group containing a C=N bond
cyanoborohydride. Since imines derived from unsymmetrical ketones are prochiral, their reduction defines a route to chiral amines. Unhindered aldimines
Imine
Chemical compound
developed also: HOCH2CH(OH)CH2OH + O2 → HOCH2CH(OH)CO2H + H2O As glycerol is prochiral, the oxidation of the two terminal alcohol groups gives distinct enantiomers
Glyceric_acid
Chemical compound
usually prepared by the acylation of benzene using valeryl chloride. Being prochiral, valerophenone undergoes enantioselective hydrogenation to the corresponding
Valerophenone
Chemical compound
to form a rhodium complex to catalyze asymmetric hydroformylation of prochiral olefins. It has been shown that high substrate concentrations as well
Kelliphite
Any chemical compound having two acyl groups bonded to the same oxygen atom
pyridine compound is a better leaving group than a carboxylate ion. For prochiral cyclic anhydrides, the alcoholysis reaction can be conducted asymmetrically
Organic_acid_anhydride
Chemical reaction which attaches an electrophile to an aromatic ring
Bischler–Napieralski reaction. Electrophilic aromatic substitutions with prochiral carbon electrophiles have been adapted for asymmetric synthesis by switching
Electrophilic aromatic substitution
Electrophilic_aromatic_substitution
Chemical reactions forming cocaine
stereoselectivity of this reaction was further investigated through study of prochiral methylene hydrogen discrimination. This is due to the extra chiral center
Biosynthesis_of_cocaine
Reduction of ketones and aldehydes to their corresponding alcohols
aluminium based Meerwein–Ponndorf–Verley reduction can be performed on prochiral ketones leading to chiral alcohols. The three main ways to achieve the
Meerwein–Ponndorf–Verley reduction
Meerwein–Ponndorf–Verley_reduction
Chemical compound
catalyst was reported in 2005 to provide isotactic polymerization of the prochiral propylene oxide PPG has many properties in common with polyethylene glycol
Polypropylene_glycol
Study of chemical compounds containing fluorine-carbon bonds
whereby only one of two possible enantiomeric products are generated from a prochiral substrate, rely on electrophilic fluorination reagents. Illustrative of
Organofluorine_chemistry
biotin-streptavidin interaction. The formed ArM can catalyze the reduction of prochiral ketones. Taking advantages of protein evolvability, different mutants
Artificial_metalloenzyme
Chemical reaction
Enantioselective ketone reductions convert prochiral ketones into chiral, non-racemic alcohols and are used heavily for the synthesis of stereodefined
Enantioselective reduction of ketones
Enantioselective_reduction_of_ketones
Organic compound containing a sulfinyl group (>SO)
then oxidize further to dimethyl sulfone. Unsymmetrical sulfides are prochiral — their oxidation gives chiral sulfoxides. The process can be performed
Sulfoxide
Chemical compounds containing C–Li bonds
HIV reverse transcriptase inhibitor. Lithium acetylide is added to a prochiral ketone to yield a chiral alcohol product. The structure of the active
Organolithium_reagent
O-methylation gives the bis-lactim. A proton is then abstracted from the prochiral position on glycine with n-BuLi. The next step decides the stereoselectivity
Schöllkopf_method
Palladium-catalysed substitution reaction
complex Enantioface exchange in the π-allyl complex Differentiation of prochiral nucleophile faces The favored method for enantiodiscrimination is largely
Tsuji–Trost_reaction
Topics referred to by the same term
can be converted to a cyclic product in one step, in the same sense as prochiral Procyclic life stage, a life stage of the Trypanosoma parasite in African
Procyclic
Chemical compound
epoxidation, which is renowned for its ability to enantioselectively transform prochiral alkenes into epoxides. Before its development, catalysts for the asymmetric
Jacobsen's_catalyst
Variation of olefin metathesis
afford a mixture of E- and Z- isomers (1:3 E/Z) in 89% yield. Although one prochiral center is present the product is racemic. Floresolide is an atropisomer
Ring-closing_metathesis
Enzyme found in humans
in an aldol condensation reaction. The citrate product is said to be prochiral. This conversion begins with the negatively charged carboxylate side chain
Citrate_synthase
Reaction in organic chemistry
chiral titanium complex (Figure 12) in asymmetric ene reactions involving prochiral glyoxylate esters. The catalyst is prepared in situ from (i-PrO)2TiX2
Ene_reaction
Reaction in organic chemistry
catalysis. Barbas' collaborator List also extended the reaction to asymmetric prochiral ketones: List and Notz also revealed that proline and 5,5-dimethyl
Proline-catalyzed aldol reactions
Proline-catalyzed_aldol_reactions
Dipolar compound
dipolarophile—if the dipolarophile is more than mono-substituted (and prochiral), up to four new stereocenters can result in the product. Azomethine ylides
Azomethine_ylide
Addition of non-molecular hydrogen to a compound
proceed with high enantioselectivities when the starting material is prochiral: RR'C=O + Me2CHOH → RR'C*H−OH + Me2C=O where RR'C*H−OH is a chiral product
Transfer_hydrogenation
imines. If the complex is chiral and non-racemic and the substrate is prochiral, an excess of a single enantiomer of a chiral product can result. Hydrogen
Hydrogenation of carbon–nitrogen double bonds
Hydrogenation_of_carbon–nitrogen_double_bonds
Chemical process for converting alkenes to aldehydes
greater than the rate of beta-hydride elimination. Hydroformylation of prochiral alkenes creates new stereocenters. Using chiral phosphine ligands, the
Hydroformylation
One of the lightest perfluoro compounds
than acetone itself. Unlike both of those ketones, trifluoroacetone is prochiral. Hydrogenation of trifluoroacetone over platinum catalyst gives trifluoroisopropanol
Trifluoroacetone
Chemical reaction
explained in terms of steric interactions between the ligand and the prochiral substrate. Consideration of these interactions has led to the development
Asymmetric_hydrogenation
Chemical compound
C2-symmetric diphosphine. Its complexes have been applied to the reduction of prochiral olefins, ketones, and imines. Knowles et al. independently reported the
DIOP
Various forms of carbon crystal lattices
isomers. One of these isomers displays a helical twist and is therefore prochiral. The P and M enantiomers have been separated. Pentamantane has nine isomers
Diamondoid
Chemical process of converting alkenes to nitriles
→ Ni(CN)2L2 + H2 Ni(R)(CN)L2 + HCN → Ni(CN)2L2 + RH Most alkenes are prochiral, and their hydrocyanation generates chiral nitriles. Conventional hydrocyanation
Hydrocyanation
Chemical compound
enantioselectivities. An enantioselective (80 to 92% ee) reduction of prochiral α,β-unsaturated esters uses Tol-BINAP complexes of copper in the presence
Copper_hydride
atropisomerism; the rigidity of the phosphene ligands can impart chirality on prochiral substrates with high fidelity, allowing for asymmetric hydrogenation.
Metal-ligand_cooperativity
Use of natural catalysts to perform chemical transformations
"recognized" upon the formation of the enzyme-substrate complex. Thus a prochiral substrate may be transformed into an optically active product and both
Biocatalysis
Chemical compound
multi-step synthesis in the construction of polycyclic natural products. It is prochiral. With strong bases, the positions 4 and 6 (the two CH2-groups of the carbonyl
Cyclohexenone
are known. These derivatives, also known as N-acylamino acrylates, are prochiral substrates for asymmetric hydrogenation. The 2001 Nobel Prize in Chemistry
Dehydroamino_acid
Synthesis of syn-α-Substituted β-Amino Ketones using Sulfinimines and Prochiral Weinreb Amide Enolates". Organic Letters. 9 (12): 2413–2416. doi:10.1021/ol0708166
N-Sulfinyl_imine
Latvian-American professor of chemistry
including protonation of carbanions, acylation and alkylation of achiral and prochiral nucleophiles, parallel kinetic resolution, and control of configuration
Edwin_Vedejs
Chemistry of iron compounds containing a carbon-to-iron chemical bond
3-hexafluoropropane as a non-coordinating solvent. Fp-R compounds are prochiral, and studies have exploited the chiral derivatives CpFe(PPh3)(CO)acyl
Organoiron_chemistry
Chemical compound
oxazolidinones. Extensive work has been reported on asymmetric hydroxylation of prochiral enolates with camphorsulfonyloxaziridine derivatives, achieving moderate
Oxaziridine
Catalyzed organic reactions that produce an organoboron compound
In 1981, Hirao and co-workers have found that asymmetric reduction of prochiral aromatic ketones with chiral amino alcohols and borane afforded the corresponding
Borylation
diphosphines such as BINAP. Styrene or its simple derivatives are usually the prochiral substrate. Enantioselectivity tends to be lowered with ortho-substituents
Metal-catalysed_hydroboration
been extensively studied. Unsymmetrical thioethers, e.g., SMeEt, are prochiral ligands, and their complexes are chiral. One example is [Ru(NH3)5(SMeEt)]2+
Transition metal thioether complex
Transition_metal_thioether_complex
Main-group allene analog
Marinetti, Angela; Ricard, Louis; Mathey, Francois (January 1992). "Use of prochiral phosphaalkene complexes in the synthesis of optically active phosphines"
1-Phosphaallenes
Ukrainian Chemist
them. The complexes were used for asymmetric homogenous hydrogenation of prochiral substrates, and the obtained results allowed elucidating the effects of
Igor_V._Komarov
different. They are neither diastereotopic or enantiotopic nor homotopic. Prochiral conformational analysis 300 MHz 1H-NMR spectrum of ethyl phenylalaninate
Topicity
Species of bacterium
can from a stereospecific carbon–carbon bond used in the synthesis of prochiral ketones which are important precursors in biofuel production. Hydrogenases
Thermotoga_maritima
Chemical compound
BM, Brennan MK (May 2006). "Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline". Organic Letters. 8 (10): 2027–30. doi:10.1021/ol060298j
Horsfiline
Chemical reaction with carbon-metal bond
alkenes to form substituted alkanes can be rendered enantioselective if prochiral alkenes are used. In these reactions, a chiral indenyl zirconium catalyst
Carbometalation
PROCHIRALITY
PROCHIRALITY
PROCHIRALITY
PROCHIRALITY
Boy/Male
German, Scandinavian
Father of Peace; Diminutive of Axel
Girl/Female
Muslim/Islamic
Honest
Girl/Female
Hindu
Tender, Good, Kind, Polite
Boy/Male
Tamil
Bibhishana | பிபீஷண
One of the chirajivins. he is one of the seven persons who r considered to be deathless
Girl/Female
Gujarati, Hindu, Indian, Kannada, Marathi, Sindhi, Tamil, Telugu
Jasmine
Biblical
name; renown
Girl/Female
Cornish American English
Fair and yielding.
Girl/Female
English American Norse
Lives in the valley. Small valley. Surname.
Girl/Female
Assamese, Bengali, Celebrity, Gujarati, Hindu, Indian, Kannada, Malayalam, Marathi, Mythological, Oriya, Sanskrit, Sindhi, Tamil, Telugu
Pleasure; Desire; Goddess Parvati; Purity
Surname or Lastname
English, Welsh, and Scottish
English, Welsh, and Scottish : variant of Morris.Dutch and North German : variant of Moritz.French : variant of Maurice.Latvian : nickname for a dark person, from Moris ‘Moor’, ‘Negro’. Compare Moore 2.Lithuanian : possibly a nickname from morỹs ‘lazy person’.
PROCHIRALITY
PROCHIRALITY
PROCHIRALITY
PROCHIRALITY
PROCHIRALITY