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Ability of a chemical reaction to produce an unequal mixture of stereoisomers
In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific
Stereoselectivity
Covalent bond joining a sugar molecule to another group
trichloroacetimidate to encourage B stereoselectivity through the gauche effect. This reasonable stereoselectivity is clear through visualization of the
Glycosidic_bond
Variation on the Wittig chemical reaction
modifying the structure of the phosphonate. They found greater (E)-stereoselectivity with the following conditions: Increasing steric bulk of the aldehyde
Horner–Wadsworth–Emmons reaction
Horner–Wadsworth–Emmons_reaction
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically
Chiral_auxiliary
Hoveyda's research focuses on the development for chemoselective and stereoselective catalysis, in particular function-oriented catalyst design. He is particularly
Amir_H._Hoveyda
Chemical compound
deal of stereoselectivity. This allows for more control over the reactions and the creation of very specific desired products. Stereoselectivity can be
Camphorsultam
Chemical reaction(s) which favor one chiral isomer over another
version: (2006–) "stereoselective synthesis". doi:10.1351/goldbook.S05990 Gal, Joseph (2012). "The Discovery of Stereoselectivity at Biological Receptors:
Enantioselective_synthesis
Formation of a thioether (–S–) compound from a thiol (–SH) and an alkene ( >C=C< )
accepted as a click chemistry reaction given the reactions' high yield, stereoselectivity, high rate, and thermodynamic driving force. The reaction results
Thiol-ene_reaction
Chemical construction of organic compounds
synthetic routes that can be completed including total synthesis, stereoselective synthesis, automated synthesis, and many more. A total synthesis refers
Organic_synthesis
Chemical reaction
Diels–Alder reactions. Many methods have been developed for influencing the stereoselectivity of the Diels–Alder reaction, such as the use of chiral auxiliaries
Diels–Alder_reaction
Pericyclic chemical reaction
influence the regioselectivity and stereoselectivity of the 1,3-dipolar cycloaddition reaction. The stereoselectivity of 1,3-dipolar cycloaddition reactions
1,3-Dipolar_cycloaddition
American chemist and Nobel Laureate (born 1941)
He is a two-time Nobel laureate in chemistry, known for his work on stereoselective reactions and click chemistry. Sharpless was awarded half of the 2001
Karl_Barry_Sharpless
Chemical reaction
previously, the hydrazones exhibit higher reactivity, regioselectivity and stereoselectivity. The combination of cyclic amino acid derivatives (SAMP and RAMP)
Enders SAMP/RAMP hydrazone-alkylation reaction
Enders_SAMP/RAMP_hydrazone-alkylation_reaction
Rule in organic chemistry
Fürst-Plattner rule (also known as the trans-diaxial effect) describes the stereoselective addition of nucleophiles to cyclohexene derivatives. Cyclohexene derivatives
Fürst-Plattner_Rule
Chemical reaction
main chain: The principal factor determining an aldol reaction's stereoselectivity is the enolizing metal counterion. Shorter metal-oxygen bonds "tighten"
Aldol_reaction
Chemical compound
group at the one carbon position. Specifically, PD1 is an endogenous stereoselective lipid mediator classified as an autocoid protectin. Autacoids are enzymatically
Protectin_D1
Chemical compound and chemical warfare nerve agent
Arie; Marcus, Dino; Velan, Baruch; Shafferman, Avigdor (2004). "Stereoselectivity toward VX is Determined by Interactions with Residues of the Acyl
VX_(nerve_agent)
phosphonates, but these reactions often proceeded in low yields and poor stereoselectivity. The original work by Toshikazu Hirao et al. was published in 1980
Hirao_coupling
Medication mainly used for depression and smoking cessation
Kraus K, Blood J, Stevens A, Miller JP, et al. (November 2020). "Stereoselective Steady-State Disposition and Bioequivalence of Brand and Generic Bupropion
Bupropion
Chemical reaction
Generation of (R,R) epoxides from corresponding alkenes increases in stereoselectivity with increased steric bulk of substituent R groups (especially in
Shi_epoxidation
Reduction of ketones and aldehydes to their corresponding alcohols
reduction. Both ruthenium and samarium have shown high yields and high stereoselectivity in the reduction of carbonyls to alcohols. The ruthenium catalyst
Meerwein–Ponndorf–Verley reduction
Meerwein–Ponndorf–Verley_reduction
Organic chemical transformations
stereocenters between the radical and multiple bond are often highly stereoselective. Radical cyclizations to form polycyclic products often take advantage
Radical_cyclization
Chemical compound
THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones to alcohols. Like other borohydrides, reductions
L-selectride
Dipolar compound
Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions
Azomethine_ylide
Type of strain energy in organic chemistry
groups. Polarity also has an effect on allylic strain. In terms of stereoselectivity, polar groups act like large, bulky groups. Even though two groups
Allylic_strain
with alkenyl diazo ketones. A mechanistic rationale for the high stereoselectivity observed in cyclopropanations catalyzed by (semicorrinato)copper complexes
Semicorrin
Medication used to treat malaria and babesiosis
quinine biosynthesis, the enzyme strictosidine synthase catalyzes a stereoselective Pictet–Spengler reaction between tryptamine and secologanin to yield
Quinine
Sub-field of organic chemistry
construct glycosidic linkages that have optimum molecular geometry (stereoselectivity) and the stable bond (regioselectivity) at the reaction site (anomeric
Carbohydrate_synthesis
Sedating antidepressant
liver via oxidation and N-demethylation. Its metabolism is highly stereoselective. Based on in vitro research, the major enzymes involved in the metabolism
Doxepin
Coupling reaction
catalytic activity in this type of reaction. This coupling reaction is stereoselective with a propensity for trans coupling as the palladium halide group
Heck_reaction
Reaction in organic chemistry
products. Using metal catalysts that have chiral ligands leads to stereoselectivity of the newly-formed carbon–carbon bond. Mundy, Bradford P.; Ellerd
Doyle–Kirmse_reaction
Psychoactive drug, often called ecstasy
to exhibit different kinetics. The disposition of MDMA may also be stereoselective, with the S-enantiomer having a shorter elimination half-life and greater
MDMA
Chemical compound
available and known for its directed hydrogenation to give trans stereoselectivity with respective of directing group. The cation has a square planar
Crabtree's_catalyst
Chemistry
formation by coordinating with the aldehyde oxygen. This greatly improves stereoselectivity and yield. Ward and his associates also found that by adding trace
Dynamic kinetic resolution in asymmetric synthesis
Dynamic_kinetic_resolution_in_asymmetric_synthesis
Chemical compound
preferentially metabolizes into α-3'-hydroxyhexobarbital, the reaction thus is stereoselective. Both enantiomers, however, form both α- and β-isomers. In total four
Hexobarbital
Chemical process
donors termed (thio)urea organocatalysis covers both non-stereoselective and stereoselective reactions. Hydrogen-bonding between thiourea derivatives
Thiourea_organocatalysis
American medicinal chemist
spanning more than 10 years. His Ph.D. thesis, published in 1989, was on stereoselective actions of psychedelics, including the lysergamides LA-Aziridine and
Robert_Oberlender
Use of squaramides as hydrogen-bond catalyst to accelerate reactions
donors termed squaramide organocatalysis covers both non-stereoselective and stereoselective applications. A squaramide organocatalyst typically contains
Squaramide_catalysis
reaction. Stereochemistry is involved in: stereospecific reactions stereoselective or asymmetric reactions racemisation processes Carey, Francis A.; Sundberg
Dynamic_stereochemistry
Cross coupling reaction in organic chemistry
In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard
Kumada_coupling
Class of chemical reaction
ring-expansion reaction. 2,3-sigmatropic rearrangements can offer high stereoselectivity. At the newly formed double bond there is a strong preference for
2,3-sigmatropic_rearrangement
Stereoisomerism found in bridged-ring compounds
terms endo and exo are used in a similar sense in discussions of the stereoselectivity in Diels–Alder reactions. IUPAC, Compendium of Chemical Terminology
Endo–exo_isomerism
Chemical compound
Hirschmann, H. (1 October 1960). "The Nature of Substrate Asymmetry in Stereoselective Reactions". Journal of Biological Chemistry. 235 (10): 2762–2767. doi:10
Glycerol
transition state is involved in metallo-ene reaction, high level of stereoselectivity can be expected due to the conservation of orbital symmetry. Indeed
Metallo-ene_reaction
Chemical reaction
variants of this transformation have been developed. To achieve the stereoselectivity, employing bidentate chiral ligand into the reactions is the most
Kharasch–Sosnovsky_reaction
Organic reduction of any carbonyl group by a reducing agent
support of the Anh?Eisenstein electronic model in controlling ?-facial stereoselectivity in nucleophilic additions to carbonyl compounds". Journal of the Chemical
Carbonyl_reduction
Medication for slow heart rate
"Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis". Open Chemistry. 18 (1): 628–647. doi:10.1515/chem-2020-0056
Isoprenaline
Anticholinergic deliriant drug
ISBN 978-1-4243-0080-8. Liu YM, Liu H, Zhong BH, Liu KL (2006). "Stereoselective Synthesis of the Optical Isomers of a New Muscarinic Receptor Antagonist
EA-3167
Ability of a chemical reaction mechanism to differentiate between stereoisomers
operates on only one (or a subset) of the stereoisomers. In contrast, stereoselectivity is the property of a reactant mixture where a non-stereospecific mechanism
Stereospecificity
Meteorite found in Victoria, Australia
according to the argument that it would be "unusual for an abiotic stereoselective decomposition or synthesis of amino acids to occur with protein amino
Murchison_meteorite
Chemical compound
mechanism, transition state geometry, and a comment on the origin of stereoselectivity". The Journal of Organic Chemistry. 42 (6): 1108–1109. doi:10.1021/jo00426a048
Sodium_borohydride
Fluorine reaction
electrophilic fluorination is currently unclear, highly efficient and stereoselective methods have been developed. Some common fluorinating agents used for
Electrophilic_fluorination
Structural analog of a ketone with selenium replacing oxygen
derivatizing agents for 77Se-NMR. Chiral oxazolidineselones can be used for stereoselective control of aldol reactions, analogous to the Evans aldol reaction that
Selone
Chemical reaction
Sharpless asymmetric dihydroxylation (also called the Sharpless bishydroxylation) is the chemical reaction of an alkene with osmium tetroxide in the presence
Sharpless asymmetric dihydroxylation
Sharpless_asymmetric_dihydroxylation
L-proline amide hydrolase (EC 3.5.1.101, S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase, LaaA, L-amino acid amidase) is an enzyme with
L-proline_amide_hydrolase
prochiral position on glycine with n-BuLi. The next step decides the stereoselectivity of the method: One face of the carbanionic center is shielded by steric
Schöllkopf_method
Organometallic compounds used in organic synthesis
ones. An example of the Grignard reaction is a key step in the (non-stereoselective) industrial production of Tamoxifen (currently used for the treatment
Grignard_reagent
Dissociative anesthetic and anti-depressant
Okawa H, Appadu BL, Grandy DK, Devi LA, Lambert DG (January 1999). "Stereoselective interaction of ketamine with recombinant mu, kappa, and delta opioid
Ketamine
Central nervous system stimulant
0.CO;2-4. Axten JM, Krim L, Kung HF, Winkler JD (1998). "A Stereoselective Synthesis of dl-threo-Methylphenidate: Preparation and Biological Evaluation
Methylphenidate
Psychedelic drug
Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE (March 1995). "Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and
LSD
enzyme aggregates with a difunctional cross-linker. They can be used as stereoselective industrial biocatalysts. Enzymes are proteins that catalyze (i.e. accelerate)
Cross-linked_enzyme_aggregate
Hybrid flowering plant in the olive family Oleaceae
in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers. Dirr
Forsythia_×_intermedia
Geometric property of some molecules and ions
1016/0040-4020(59)80014-4. Gal, Joseph (2012). "The Discovery of Stereoselectivity at Biological Receptors: Arnaldo Piutti and the Taste of the Asparagine
Chirality_(chemistry)
Organic compound of the form >C(OH)O–
be synthesized from nucleophilic addition to hemiacetals with high stereoselectivity, which can be further used to form polymers such as lignans. Hemiacetals
Hemiacetal
Conversion of an enantiomer to its mirror image
S2CID 30916093. Ariëns EJ, Wuis EW, Veringa EJ (January 1988). "Stereoselectivity of bioactive xenobiotics. A pre-Pasteur attitude in medicinal chemistry
Chiral_inversion
Chemical compound
Geranylfarnesol Jin, Yinghua; Roberts, Frank G.; Coates, Robert M. (2007). "Stereoselective Isoprenoid Chain Extension with Acetoacetate Dianion: [(E, E, E)-Geranylgeraniol
Geranylgeraniol
Molecules which are non-mirror image, non-identical stereoisomers
one diastereomer over the other in an organic reaction. In general, stereoselectivity is attributed to torsional and steric interactions in the stereocenter
Diastereomer
Chemical reaction
enolate oxygens and the electrophile, which explains its high anti‑stereoselectivity. The reaction was first reported by Bulgarian organic chemist, Academician
Ivanov_reaction
accounts for the importance of the alpha amino group and the absence of stereoselectivity on chiral reaction sites. 1,2,3-Triazole and related heterocycles
Bruylants_reaction
Chemical compound
doi:10.1038/nchem.1351. PMID 22717438. Giese B (August 1989). "The Stereoselectivity of Intermolecular Free Radical Reactions [New Synthetic Methods (78)]"
Tunicamycin
Chemical group (–CH2–CH3)
ethyl substituent are diastereotopic. Chiral reagents are known to stereoselectively modify such substituents. The name of the group is derived from the
Ethyl_group
Chemical compounds containing C–Li bonds
alcohol. Addition of lithium salts such as LiClO4 can improve the stereoselectivity of the reaction. When the ketone is sterically hindered, using Grignard
Organolithium_reagent
Chemical compound
Francis. pp. 9–46. Matveeva, E. D.; et al. (1995). "Regioselective and stereoselective substitution of hydroxyl group for halogen in allyl alcohols". Russian
Trichloroacetonitrile
Chemical compound (CH3SO2Cl)
1016/0008-6215(83)88490-0. Merlin, P.; Braekman, J. C.; Daloze, D. (1988). "Stereoselective synthesis of (±)-tetraponerine-8, a defence alkaloid of the ant Tetraponera
Methanesulfonyl_chloride
Chemical agent and drug construction
In 2001, Gilbert Stork of Columbia University published the first stereoselective total synthesis of quinine. The primary focus of the synthesis was
Quinine_total_synthesis
Chemical compound
through which LSD exerts most of its pharmacological effects, with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing
Lysergic_acid_2-butylamide
Chemical reaction
3-aryl-3-hydroxyisoindolin-1-ones in 2019. The reaction yields a high stereoselectivity under high temperature as the adjacent quaternary and stereogenic
Ketimine_Mannich_reaction
Anticholinergic medication used as antidote for nerve agent poisoning
atropine is present as (+)-hyoscyamine was found, suggesting that stereoselective metabolism of atropine probably occurs. Effects on the iris and ciliary
Atropine
Chemical reaction mechanism
"Organocatalytic regio- and asymmetric C-selective S(N)Ar reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3'-oxoindoles". Journal
Nucleophilic aromatic substitution
Nucleophilic_aromatic_substitution
Pregnancy prevention methods used by men
Jin Z, et al. (May 2022). "Discovery of potent BET bromodomain 1 stereoselective inhibitors using DNA-encoded chemical library selections". Proceedings
Male_contraceptive
Subdiscipline of chemistry
József Nagy, Gábor Hornyánszky, Zoltán Boros Stereochemistry and Stereoselective Synthesis: An Introduction 2016 ISBN 3527339019 "the definition of
Stereochemistry
Chemical reaction
without existing stereocenters, Bartlett and coworkers found that stereoselectivity was achievable. They were able to synthesize the cis and trans five
Iodolactonization
Class of compounds in the nervous system
Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorg Med Chem
Monoaminergic activity enhancer
Monoaminergic_activity_enhancer
Short-acting anaesthetic and sedative drug
University Press. Tomlin SL, Jenkins A, Lieb WR, Franks NP (March 1998). "Stereoselective effects of etomidate optical isomers on gamma-aminobutyric acid type
Etomidate
Chemical reaction to produce organic compounds
Bidentate phosphine ligands are common in asymmetric reactions to enhance stereoselectivity. A wide variety of bases may be used, and the base is often employed
Intramolecular_Heck_reaction
Chemical reaction
"Samarium-catalyzed intramolecular Tishchenko reduction of β-hydroxy ketones. A stereoselective approach to the synthesis of differentiated anti 1,3-diol monoesters"
Evans–Tishchenko_reaction
German chemist (1943–2026)
research focused on directed evolution, enzymes in organic chemistry, and stereoselective biocatalysis. Reetz was born in Hirschberg, Gau Lower Silesia on 13
Manfred_T._Reetz
Organic anion formed by deprotonating a carbonyl (>C=O) compound
ketones and E enolates from esters, but HMPA is known to reverse the stereoselectivity of deprotonation. Likewise different Lewis acids give different enolate
Enolate
Organic chemist
as well as the first natural product to be synthesised with high stereoselectivity. Stork was also a mentor of young chemists with many of his students
Gilbert_Stork
Product made by or of life forms
were detected. It is also possible for polyisoprenoid chains to be stereoselectively synthesised using catalysts such as Al(C2H5)3 – VCl3. However, the
Biogenic_substance
Pain medication of the opiate family
C6, C9, C13, and C14) with morphine exhibiting a high degree of stereoselectivity of analgesic action."[better source needed][needs update] Morphine
Morphine
Uniformity of handedness
the inverse stereoselectivity is observed for L-RNA. Once homochiral peptides are produced from homochiral nucleic acids, stereoselectively could subsequently
Homochirality
Interactions between atomic groups on different parts of a ring molecule
S2CID 250856875. Greve, Björn; Imming, Peter (1997). "Regio- and Stereoselectivity of Water Elimination as a Function of Ring Size". Journal of Organic
Prelog_strain
Short chains of 2–50 amino acids
Marc; Javor, Sacha; Darbre, Tamis; Reymond, Jean-Louis (2019-08-21). "Stereoselective pH Responsive Peptide Dendrimers for siRNA Transfection". Bioconjugate
Peptide
Charged chemical group of the form >CO–
(2019-04-18). "Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations". ACS Central Science. 5 (5): 781–788. doi:10
Oxocarbenium
Inhalational anesthetic
PMID 17456811. Bu W, Pereira LM, Eckenhoff RG, Yuki K (6 May 2014). "Stereoselectivity of isoflurane in adhesion molecule leukocyte function-associated antigen-1"
Isoflurane
Medical device
Ruiqing; Balijepalli, Anant; Hamoud, Aladin; Grinstaff, Mark W. (2022). "Stereoselective [2+2] Cycloadditions: Synthesis of a Tri-O-Bn-D-Glucal-derived β-Lactam"
Syringe_driver
Chemical reaction used in organic chemistry
regioselectivity of the elimination step, and improving the overall stereoselectivity. These have been successful to varying degrees. Additionally, modifications
Nazarov_cyclization
Tropane alkaloid and stimulant drug
impractical due to its high cost, low efficiency, and challenges in stereoselective synthesis compared to extraction from natural plant sources. While
Cocaine
of BINOL as in Tagliavini's procedure. Keck's early success with stereoselectivity and the simplicity of the catalyst preparation led to many improvements
Keck_asymmetric_allylation
STEREOSELECTIVITY
STEREOSELECTIVITY
STEREOSELECTIVITY
STEREOSELECTIVITY
Boy/Male
Hindu, Indian
Glorious
Girl/Female
Teutonic
Holy spirit of the forest.
Girl/Female
Indian, Sanskrit, Telugu
Vedas; Weapon
Boy/Male
American, Australian, Christian, Hebrew, Irish, Latin, Swedish
Peaceful; Prayed for; Sun
Girl/Female
Muslim
Olive, Fiery, Sower of seeds
Male
Scandinavian
 Scandinavian form of Old Norse Haraldr, HARALD means "army ruler." Compare with another form of Harald.
Surname or Lastname
English
English : habitational name from any of numerous places so called from Old English lang ‘long’ + tūn ‘enclosure’, ‘settlement’. (Langton in County Durham, however, has the same etymology as Langdon).
Boy/Male
Hindu
Beautiful Moon
Biblical
bone of a bone; our strength
Girl/Female
Tamil
Silver, A companion
STEREOSELECTIVITY
STEREOSELECTIVITY
STEREOSELECTIVITY
STEREOSELECTIVITY
STEREOSELECTIVITY