Cargando…

Metal–Organic Frameworks Invert Molecular Reactivity: Lewis Acidic Phosphonium Zwitterions Catalyze the Aldol-Tishchenko Reaction

[Image: see text] The influence of metal–organic frameworks (MOFs) as additives is herein described for the reaction of n-alkyl aldehydes in the presence of methylvinylketone and triphenylphosphine. In the absence of a MOF, the expected Morita–Baylis–Hillman product, a β-hydroxy enone, is observed....

Descripción completa

Detalles Bibliográficos
Autores principales:	Bauer, Gerald, Ongari, Daniele, Xu, Xiaoying, Tiana, Davide, Smit, Berend, Ranocchiari, Marco
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2017
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742478/ https://www.ncbi.nlm.nih.gov/pubmed/29198106 http://dx.doi.org/10.1021/jacs.7b10928

Ejemplares similares

Mechanism and Origins of Stereoselectivity of the Aldol-Tishchenko Reaction of Sulfinimines
por: Turlik, Aneta, et al.
Publicado: (2021)

Metal-organic frameworks as kinetic modulators for branched selectivity in hydroformylation
por: Bauer, Gerald, et al.
Publicado: (2020)

Enantioselective Evans-Tishchenko Reduction of β-Hydroxyketone Catalyzed by Lithium Binaphtholate
por: Ichibakase, Tomonori, et al.
Publicado: (2011)

Stereoselective Installation of Five Contiguous Stereogenic Centers in a Double Aldol–Tishchenko Cascade and Evaluation of the Key Transition State through DFT Calculation
por: Mackey, Pamela, et al.
Publicado: (2021)

A Zwitterionic Phosphonium Stannate(II) via Hydrogen Splitting by a Sn/P Frustrated Lewis‐Pair and Reductive Elimination
por: Holtkamp, Philipp, et al.
Publicado: (2020)

Origin of the Strong Interaction between Polar Molecules and Copper(II) Paddle-Wheels in Metal Organic Frameworks
por: Ongari, Daniele, et al.
Publicado: (2017)

Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins
por: Ismiyarto,, et al.
Publicado: (2021)

Too Many Materials and Too Many Applications: An Experimental Problem Waiting for a Computational Solution
por: Ongari, Daniele, et al.
Publicado: (2020)

Kinetics versus thermodynamics in the proline catalyzed aldol reaction
por: Orlandi, M., et al.
Publicado: (2016)

Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol
por: Farrar, Elliot H. E., et al.
Publicado: (2022)

Applicability of Tail Corrections in the Molecular Simulations of Porous Materials
por: Jablonka, Kevin Maik, et al.
Publicado: (2019)

Building a Consistent and Reproducible Database for Adsorption Evaluation in Covalent–Organic Frameworks
por: Ongari, Daniele, et al.
Publicado: (2019)

Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates
por: Kawanishi, Ryouta, et al.
Publicado: (2019)

Vinylene‐Linked Covalent Organic Frameworks by Base‐Catalyzed Aldol Condensation
por: Acharjya, Amitava, et al.
Publicado: (2019)

Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes
por: Kennington, Stuart C. D., et al.
Publicado: (2021)

Tyramine Derivatives Catalyze the Aldol Dimerization of Butyraldehyde in the Presence of Escherichia coli
por: Dennis, Jonathan A., et al.
Publicado: (2022)

Big-Data Science in Porous Materials: Materials Genomics and Machine Learning
por: Jablonka, Kevin Maik, et al.
Publicado: (2020)

Enantioselective Aldol Addition of Acetaldehyde to Aromatic Aldehydes Catalyzed by Proline-Based Carboligases
por: Saifuddin, Mohammad, et al.
Publicado: (2020)

Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis
por: Miskov‐Pajic, Vukoslava, et al.
Publicado: (2020)

Phosphonium-Templated Iodoplumbates
por: Omahen, Emily H., et al.
Publicado: (2018)

Thermoelasticity of Flexible Organic Crystals from Quasi-harmonic Lattice Dynamics: The Case of Copper(II) Acetylacetonate
por: Maul, Jefferson, et al.
Publicado: (2020)

Asymmetric Aldol Reactions of α,β-Unsaturated Ketoester Substrates Catalyzed by Chiral Diamines
por: Kan, Sha-Sha, et al.
Publicado: (2011)

Diversifying Databases of Metal Organic Frameworks for High-Throughput Computational Screening
por: Majumdar, Sauradeep, et al.
Publicado: (2021)

Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis
por: Tan, Jian-Ping, et al.
Publicado: (2022)

Comparison of L-Threonine Aldolase Variants in the Aldol and Retro-Aldol Reactions
por: Fesko, Kateryna
Publicado: (2019)

Design of Phosphonium-Type Zwitterion as an Additive to Improve Saturated Water Content of Phase-Separated Ionic Liquid from Aqueous Phase toward Reversible Extraction of Proteins
por: Ito, Yoritsugu, et al.
Publicado: (2013)

Cyclic phosphonium ionic liquids
por: Lall-Ramnarine, Sharon I, et al.
Publicado: (2014)

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO(2) with Epoxides Catalyzed by Phenol‐Functionalized Phosphonium Salts
por: Hu, Yuya, et al.
Publicado: (2020)

Accurate Characterization of the Pore Volume in Microporous Crystalline Materials
por: Ongari, Daniele, et al.
Publicado: (2017)

Rapid and Efficient Functionalized Ionic Liquid-Catalyzed Aldol Condensation Reactions Associated with Microwave Irradiation
por: Wang, Chang, et al.
Publicado: (2014)

Efficient synthesis of C(15) fuel precursor by heterogeneously catalyzed aldol-condensation of furfural with cyclopentanone
por: Ao, Lei, et al.
Publicado: (2019)

Evaluating Charge Equilibration Methods To Generate Electrostatic Fields in Nanoporous Materials
por: Ongari, Daniele, et al.
Publicado: (2018)

Nanoporous Aluminosilicate-Catalyzed Telescoped Acetalization-Direct Aldol Reactions of Acetals with 1,3-Dicarbonyl Compounds
por: Davies, Thomas Edward, et al.
Publicado: (2018)

Nonanal Gas Sensors Using Porous Glass as a Reaction Field for Ammonia-Catalyzed Aldol Condensation
por: Tsujiguchi, Masato, et al.
Publicado: (2023)

Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction
por: Rodríguez-Franco, Carlos, et al.
Publicado: (2023)

Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone
por: Isoda, Motoyuki, et al.
Publicado: (2022)

Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential
por: Rohman, Nur, et al.
Publicado: (2023)

N-Geminal P/Al Lewis Pair–Alkyne Dipolar Cycloaddition to the Zwitterionic C(2)PNAl-Heterocyclopentene
por: Ding, Shuang, et al.
Publicado: (2017)

Zwitterion Nondetergent Sulfobetaine-Modified SnO(2) as an Efficient Electron Transport Layer for Inverted Organic Solar Cells
por: Tran, Van-Huong, et al.
Publicado: (2019)

Ferrocene-Containing Sterically Hindered Phosphonium Salts
por: Ermolaev, Vadim, et al.
Publicado: (2018)

Cannot write session to /tmp/vufind_sessions/sess_357ean1b7ot44dbp1cj3bmu69a