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Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space.

ABSTRACT: The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji-Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds.

SUBMITTER: Herbert SA

PROVIDER: S-EPMC4273304 | biostudies-other | 2014

REPOSITORIES: biostudies-other

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Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space.

Herbert Simon A SA van Laeren Laura J LJ Castell Dominic C DC Arnott Gareth E GE

Beilstein journal of organic chemistry 20141125

The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji-Trost allylation reaction, returning results comparable to their plana ...[more]

PMID: 25550740

Similar Datasets

Correction: Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space.

Project description:[This corrects the article DOI: 10.3762/bjoc.10.291.].

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Synthesis of deep-cavity fluorous calix[4]arenes as molecular recognition scaffolds.

Project description:Several lower-rim perfluoroalkylated (fluorous) calix[4]arenes have been synthesized by O-alkylation of the parent calix[4]arene. The compounds are formed in the cone conformation. They are soluble in several fluorous solvents and show promise for use in sensing, selective extractions and other applications.

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Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts.

Project description:A new class of recyclable supported chiral heterogeneous ligands has been synthesized by the reaction of functionalized mesoporous SBA-15 with aliphatic- and aromatic-substituted chiral amino oxazoline ligands. The obtained chiral heterogeneous ligands were characterized by several techniques such as Fourier transform infrared, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and BET-BJH. The application of these new heterogeneous ligands in copper-catalyzed asymmetric allylic oxidation of olefins by using perester showed better yields up to 95% and better enantioselectivities up to 96% compared to the corresponding homogeneous catalysts. These findings can be considered as an important step in the advancement of green chemistry. Investigation of the recyclability of the catalysts confirmed that they were easily recovered and reused eight times without significant losses in reactivity, yield, and enantioselectivity.

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Anion responsive TTF-appended calix[4]arenes. Synthesis and study of two different conformers.

Project description:Two new cone- and 1,3-alternate-calix[4]arenes (cone-1 and 1,3-alt-1), bearing four modified TTF (tetrathiafulvalene) substituents on the upper rim, have been synthesized. The binding ability of these two sets of conformers for various anions, including F(-), Cl(-), Br(-), I(-), PF6(-), ClO4(-), HSO4(-), CH3COO(-), H2PO4(-), and HP2O7(3-), was tested in organic media by monitoring the changes in their UV/vis and (1)H NMR spectra as a function of added anion, as well as via cyclovoltammetry (CV) (all anions studied as their respective TBA salts). On the basis of the present findings, we propose that incorporation of four TTF units within an overall calix[4]arene-based recognition framework produces a preorganized receptor system that displays a modest preference for the pyrophosphate (HP2O7(3-)) anion.

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Synthesis of Ultrastable and Bioconjugable Ag, Au, and Bimetallic Ag_Au Nanoparticles Coated with Calix[4]arenes.

Project description:Compared to gold nanoparticles, silver nanoparticles are largely underexploited for the development of plasmonic nanosensors. This is mainly due to their easy chemical degradation through oxidation, poor colloidal stability, and usually broad size distribution after synthesis, which leads to broad localized surface plasmon resonance bands. Coatings based on polymers such as poly(ethylene glycol) (PEG) or poly(vinylpyrrolidone) (PVP) and plant extracts have been used for the stabilization of AgNPs; however, these thick coatings are not suitable for sensing applications as they isolate the metallic core. The examples of stable AgNPs coated with a thin organic layer remain scarce in comparison to their gold counterparts. In this work, we present a convenient one-step synthesis strategy that allows to obtain unique gold, silver, and bimetallic NPs that combine all of the properties required for biosensing applications. The NPs are stabilized by a tunable calix[4]arene-based monolayer obtained through the reduction of calix[4]arene-tetradiazonium salts. These multidentate ligands are of particular interest as (i) they provide excellent colloidal and chemical stabilities to the particles thanks to their anchoring to the surface via multiple chemical bonds, (ii) they allow the subsequent (bio)conjugation of (bio)molecules under mild conditions, and (iii) they allow a control over the composition of mixed coating layers. Ag and Ag_Au nanoparticles of a high stability are obtained, opening perspectives for development of numerous biosensing applications.

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Adenine oligomer directed synthesis of chiral gold nanoparticles.

Project description:Precise control of morphology and optical response of 3-dimensional chiral nanoparticles remain as a significant challenge. This work demonstrates chiral gold nanoparticle synthesis using single-stranded oligonucleotide as a chiral shape modifier. The homo-oligonucleotide composed of Adenine nucleobase specifically show a distinct chirality development with a dissymmetric factor up to g ~ 0.04 at visible wavelength, whereas other nucleobases show no development of chirality. The synthesized nanoparticle shows a counter-clockwise rotation of generated chiral arms with approximately 200 nm edge length. The molecular dynamics and density functional theory simulations reveal that Adenine shows the highest enantioselective interaction with Au(321)R/S facet in terms of binding orientation and affinity. This is attributed to the formation of sequence-specific intra-strand hydrogen bonding between nucleobases. We also found that different sequence programming of Adenine-and Cytosine-based oligomers result in chiral gold nanoparticles' morphological and optical change. These results extend our understanding of the biomolecule-directed synthesis of chiral gold nanoparticles to sequence programmable deoxyribonucleic acid and provides a foundation for programmable synthesis of chiral gold nanoparticles.

| S-EPMC9250518 | biostudies-literature

Synthesis of Chiral Helic[1]triptycene[3]arenes and Their Enantioselective Recognition Towards Chiral Guests Containing Aminoindan Groups.

Project description:Starting from the enantiopure precursors, a pair of chiral macrocyclic arenes named helic[1]triptycene[3]arenes were conveniently synthesized. The circular dichroism (CD) spectra of the enantiomeric macrocyclic arenes exhibited mirror images, and the X-ray single crystal structures confirmed their absolute conformations as well. Moreover, the macrocyclic arenes showed strong complexation with secondary ammonium and primary ammonium salts containing aminoindan groups. In particular, the chiral macrocyclic arenes exhibited enantioselective recognition ability towards the chiral secondary ammonium salts containing aminoindan groups with an enantioselective ratio up to 3.89.

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Synthesis, immobilization and catalytic activity of a copper(II) complex with a chiral bis(oxazoline).

Project description:A chiral bis(oxazoline) bearing CH2OH groups was synthesized from a commercial bis(oxazoline) and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copper(II) complex was immobilized onto the surface of a mesoporous carbonaceous material (Starbon® 700) in which the double bonds had been activated via conventional bromination. The materials were characterized by elemental analysis, ICP-OES, XPS, thermogravimetry and nitrogen adsorption at 77 K. The new copper(II) bis(oxazoline) was tested both in the homogeneous phase and once immobilized onto a carbonaceous support for the kinetic resolution of hydrobenzoin. Both were active, enantioselective and selective in the mono-benzoylation of hydrobenzoin, but better enantioselectivities were obtained in the homogeneous phase. The heterogeneous catalyst could be separated from the reaction media at the end of the reaction and reused in another catalytic cycle, but with loss of product yield and enantioselectivity.

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Luminescence Properties of Self-Aggregating TbIII-DOTA-Functionalized Calix[4]arenes.

Project description:Self-aggregating calix[4]arenes carrying four DOTA ligands on the upper rim for stable complexation of paramagnetic GdIII-ions have already been proposed as MRI probes. In this work, we investigate the luminescence properties of TbIII-DOTA-calix[4]arene-4OPr containing four propyl-groups and compare them with those of the analog substituted with a phthalimide chromophore (TbIII-DOTA-calix[4]arene-3OPr-OPhth). We show that, given its four aromatic rings, the calix[4]arene core acts as an effective sensitizer of Tb-centered luminescence. Substituents on the lower rim can modulate the aggregation behavior, which in turn determines the luminescence properties of the compounds. In solid state, the quantum yield of the phthalimide derivative is almost three times as high as that of the propyl-functionalized analog demonstrating a beneficial role of the chromophore on Tb-luminescence. In solution, however, the effect of the phthalimide group vanishes, which we attribute to the large distance between the chromophore and the lanthanide, situated on the opposite rims of the calix[4]arene. Both quantum yields and luminescence lifetimes show clear concentration dependence in solution, related to the strong impact of aggregation on the luminescence behavior. We also evidence the variability in the values of the critical micelle concentration depending on the experimental technique. Such luminescent calix[4]arene platforms accommodating stable lanthanide complexes can be considered valuable building blocks for the design of dual MR/optical imaging probes.

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Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

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