Cargando…

Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

The synthesis of the stable surrogates of an important amino acid (R)-4-amino-3-hydroxybutyric acid (GABOB) such as substituted hydroxy aminophosphonic acids bearing a quaternary stereogenic center is presented. Highly diastereoselective formations of fluorinated spiroepoxy alkylphosphonate or relat...

Descripción completa

Detalles Bibliográficos
Autores principales:	Rapp, Magdalena, Margas-Musielak, Klaudia, Kaczmarek, Patrycja, Witkowska, Agnieszka, Cytlak, Tomasz, Siodła, Tomasz, Koroniak, Henryk
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Frontiers Media S.A. 2021
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8208234/ https://www.ncbi.nlm.nih.gov/pubmed/34150715 http://dx.doi.org/10.3389/fchem.2021.613633

Ejemplares similares

Functionalization of α-hydroxyphosphonates as a convenient route to N-tosyl-α-aminophosphonates
por: Cytlak, Tomasz, et al.
Publicado: (2018)

Diastereoselective synthesis of vicinal tertiary and N-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes
por: Goldfogel, Matthew J., et al.
Publicado: (2016)

Naphthalene vs. Benzene as a Transmitting Moiety: Towards the More Sensitive Trifluoromethylated Molecular Probes for the Substituent Effects
por: Sokół, Adam, et al.
Publicado: (2022)

Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of α-hydroxyphosphonates induced by deoxyfluorinating reagents
por: Kaczmarek, Patrycja, et al.
Publicado: (2018)

Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom
por: Aupic, Clara, et al.
Publicado: (2019)

Direct Access to Substituted 4-CF(3) β-Lactams at the C-3 Position
por: Skibińska, Monika, et al.
Publicado: (2019)

Origin of alkylphosphonic acids in the interstellar medium
por: Turner, Andrew M., et al.
Publicado: (2019)

A convergent fragment coupling strategy to access quaternary stereogenic centers
por: Kerkovius, Jeff K., et al.
Publicado: (2023)

Mechanistic insights into rhodium-catalyzed enantioselective allylic alkylation for quaternary stereogenic centers
por: Pareek, Monika, et al.
Publicado: (2020)

1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation
por: Cypryk, Marek, et al.
Publicado: (2018)

An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes
por: Aldoshin, Alexander S., et al.
Publicado: (2021)

Construction of a quaternary stereogenic center by asymmetric hydroformylation: a straightforward method to prepare chiral α-quaternary amino acids
por: Zhang, Dequan, et al.
Publicado: (2022)

Effect of Perfluoroalkyl Endgroups on the Interactions of Tri-Block Copolymers with Monofluorinated F-DPPC Monolayers
por: Shah, Syed W. H., et al.
Publicado: (2017)

Stereogenic Centers
por: Baeza, Alejandro
Publicado: (2018)

Chiral Brønsted acid-catalyzed intramolecular S(N)2′ reaction for enantioselective construction of a quaternary stereogenic center
por: Shimizu, Masahiro, et al.
Publicado: (2018)

H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
por: Niedbała, Patryk, et al.
Publicado: (2022)

Diastereoselective C-alkylation of aldimines, derived from chiral α-carbon heteroatom-substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines
por: Fuentes-Ríos, David, et al.
Publicado: (2023)

The Hydrolytic Stability and Degradation Mechanism of a Hierarchically Porous Metal Alkylphosphonate Framework
por: Lv, Kai, et al.
Publicado: (2018)

One‐step Oxidative Monofluorination of Electron‐Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
por: Berreur, Jordan, et al.
Publicado: (2022)

Friedel–Crafts-type reaction of pyrene with diethyl 1-(isothiocyanato)alkylphosphonates. Efficient synthesis of highly fluorescent diethyl 1-(pyrene-1-carboxamido)alkylphosphonates and 1-(pyrene-1-carboxamido)methylphosphonic acid
por: Wrona-Piotrowicz, Anna, et al.
Publicado: (2015)

Access to 2-Fluorinated Aziridine-2-phosphonates from α,α-Halofluorinated β-Iminophosphonates—Spectroscopic and Theoretical Studies †
por: Klarek, Mateusz, et al.
Publicado: (2023)

Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions
por: Ota, Kenji, et al.
Publicado: (2023)

High Performance Heteroatoms Quaternary-doped Carbon Catalysts Derived from Shewanella Bacteria for Oxygen Reduction
por: Guo, Zhaoyan, et al.
Publicado: (2015)

Impact of Perfluoro and Alkylphosphonic Self-Assembled Monolayers on Tribological and Antimicrobial Properties of Ti-DLC Coatings
por: Cichomski, Michal, et al.
Publicado: (2019)

Organocatalytic DYKAT of Si-Stereogenic Silanes
por: Zhou, Hui, et al.
Publicado: (2023)

Enantioselective Allylation of Stereogenic Nitrogen Centers
por: Zaitseva, Snizhana, et al.
Publicado: (2023)

Microwave-Assisted Ionic Liquid-Catalyzed Selective Monoesterification of Alkylphosphonic Acids—An Experimental and a Theoretical Study
por: Harsági, Nikoletta, et al.
Publicado: (2021)

Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin
por: D’Acquarica, Ilaria, et al.
Publicado: (2010)

Organocatalytic asymmetric synthesis of P-stereogenic molecules
por: Liu, Junyang, et al.
Publicado: (2023)

Metal Stereogenicity in Asymmetric Transition Metal Catalysis
por: Steinlandt, Philipp S., et al.
Publicado: (2023)

Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers
por: Zhang, Xin, et al.
Publicado: (2023)

Synthesis of P-Stereogenic Benzoazaphosphole 1-Oxides via Alkynylation of P-Stereogenic ortho-Aurated and ortho-Iodo Phosphinic Amides
por: Soengas, Raquel, et al.
Publicado: (2018)

A Silicon‐Stereogenic Silanol ‐ (18)O‐Isotope Labeling and Stereogenic Probe Reveals Hidden Stereospecific Water Exchange Reaction
por: Langenohl, Felix, et al.
Publicado: (2022)

Expanding the Monolayer Scope for Nucleic Acid-Based Electrochemical Sensors Beyond Thiols on Gold: Alkylphosphonic Acids on ITO
por: Shaver, Alexander, et al.
Publicado: (2023)

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
por: Kaźmierczak, Marcin, et al.
Publicado: (2020)

Nucleotide Analogues Bearing a C2′ or C3′-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors †
por: Manchoju, Amarender, et al.
Publicado: (2022)

The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
por: Moshnenko, Nazar, et al.
Publicado: (2022)

Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers
por: Zhou, Hui, et al.
Publicado: (2022)

Photocatalytic deracemisation of cobalt(iii) complexes with fourfold stereogenicity
por: Schmidt, Tanno A., et al.
Publicado: (2022)

Inductive or Field Substituent Effect? Quantum Chemical Modeling of Interactions in 1-Monosubstituted Bicyclooctane Derivatives
por: Szatylowicz, Halina, et al.
Publicado: (2017)

Cannot write session to /tmp/vufind_sessions/sess_lcnli3f01qjhuepbj92rj2dhq5