Cargando…

Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles

[Image: see text] Allylboronic esters react readily with carbonyls and imines (π-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electr...

Descripción completa

Detalles Bibliográficos
Autores principales:	García-Ruiz, Cristina, Chen, Jack L.-Y., Sandford, Christopher, Feeney, Kathryn, Lorenzo, Paula, Berionni, Guillaume, Mayr, Herbert, Aggarwal, Varinder K.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2017
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5682599/ https://www.ncbi.nlm.nih.gov/pubmed/29028321 http://dx.doi.org/10.1021/jacs.7b10240

Ejemplares similares

Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)
por: Le, Hai, et al.
Publicado: (2014)

Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles
por: Wang, Hui, et al.
Publicado: (2020)

Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
por: O'Brien, Luke, et al.
Publicado: (2022)

Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes
por: Lin, Patricia C., et al.
Publicado: (2023)

Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters
por: Kischkewitz, Marvin, et al.
Publicado: (2018)

Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes
por: Shen, Feng, et al.
Publicado: (2020)

Radical boron migration of allylboronic esters
por: Tao, Xiangzhang, et al.
Publicado: (2022)

Stereospecific Isomerization of Allylic Halides via Ion Pairs with Induced Noncovalent Chirality
por: Martinez-Erro, Samuel, et al.
Publicado: (2020)

Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications
por: Salman, Muhammad, et al.
Publicado: (2020)

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols
por: Jia, Xue-Gong, et al.
Publicado: (2017)

Potassium [1-(tert-butoxycarbonyl)-1H-indol-3-yl]trifluoroborate hemihydrate
por: Berionni, Guillaume, et al.
Publicado: (2012)

Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]‐Meisenheimer Rearrangements
por: Yu, Xin, et al.
Publicado: (2020)

Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
por: Ganesh, Venkataraman, et al.
Publicado: (2018)

Synthesis of α,γ-Chiral Trifluoromethylated Amines through the Stereospecific Isomerization of α-Chiral Allylic Amines
por: García-Vázquez, Víctor, et al.
Publicado: (2022)

Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts
por: Cahard, Elise, et al.
Publicado: (2015)

5-[(E)-Methoxy(phenyl)methylidene]-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole
por: Maji, Biplab, et al.
Publicado: (2012)

Palladium-Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones**
por: Raducan, Mihai, et al.
Publicado: (2012)

Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration
por: Jonker, Sybrand J. T., et al.
Publicado: (2020)

Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
por: Jana, Kalipada, et al.
Publicado: (2022)

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
por: Cumpstey, Ian, et al.
Publicado: (2011)

Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
por: Ashraf, Muhammad Awais, et al.
Publicado: (2021)

Experimental and computational studies of the mechanism of iron-catalysed C–H activation/functionalisation with allyl electrophiles
por: DeMuth, Joshua C., et al.
Publicado: (2021)

An expeditious route to sterically encumbered nonproteinogenic α-amino acid precursors using allylboronic acids
por: Sahu, Samrat, et al.
Publicado: (2022)

A quantitative reactivity scale for electrophilic fluorinating reagents
por: Rozatian, Neshat, et al.
Publicado: (2018)

Stereospecific Cross-Coupling Reactions of Aryl-Substituted Tetrahydrofurans, Tetrahydropyrans, and Lactones
por: Tollefson, Emily J., et al.
Publicado: (2014)

Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers and Esters
por: Tollefson, Emily J., et al.
Publicado: (2015)

Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine
por: Walter, Christopher, et al.
Publicado: (2019)

Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
por: Alam, Rauful, et al.
Publicado: (2016)

Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene
por: Ye, Yang, et al.
Publicado: (2022)

Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones
por: Turnbull, Ben W. H., et al.
Publicado: (2017)

Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids
por: Rozatian, Neshat, et al.
Publicado: (2020)

Chromoselective access to Z- or E- allylated amines and heterocycles by a photocatalytic allylation reaction
por: Martínez-Gualda, Ana María, et al.
Publicado: (2019)

Activation of Electrophile/Nucleophile Pair by a Nucleophilic and Electrophilic Solvation in a S(N)Ar Reaction
por: Sánchez, Bruno, et al.
Publicado: (2018)

Enantiospecific Synthesis of ortho‐Substituted 1,1‐Diarylalkanes by a 1,2‐Metalate Rearrangement/anti‐S(N)2′ Elimination/Rearomatizing Allylic Suzuki–Miyaura Reaction Sequence
por: Rubial, Belén, et al.
Publicado: (2018)

Developing HIV-1 Protease Inhibitors through Stereospecific Reactions in Protein Crystals
por: Olajuyigbe, Folasade M., et al.
Publicado: (2016)

Pressure Dependent Product Formation in the Photochemically Initiated Allyl + Allyl Reaction
por: Seidel, Lars, et al.
Publicado: (2013)

Rh-catalyzed regio-switchable cross-coupling of gem-difluorinated cyclopropanes with allylboronates to structurally diverse fluorinated dienes
por: Zeng, Yaxin, et al.
Publicado: (2022)

Stoichiometric Reactions of Acylnickel(II) Complexes with Electrophiles and the Catalytic Synthesis of Ketones
por: Wotal, Alexander C., et al.
Publicado: (2014)

Quantification of the Electrophilicities of Diazoalkanes: Kinetics and Mechanism of Azo Couplings with Enamines and Sulfonium Ylides
por: Li, Le, et al.
Publicado: (2022)

Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
por: Hewitt, Kirsten A., et al.
Publicado: (2022)

Cannot write session to /tmp/vufind_sessions/sess_bkg33eth8e1bh2n8a0phps3kpp