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Showing 1 to 20 of 24 for “"BINOL"”.
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BINOL-Catalyzed Asymmetric Synthesis of Chiral Heterocycles; Experimental Mechanistic Study of Binol-Catalyzed Conjugate Addition of Vinylboronic Acids to Enones; Enantioselective Synthesis of Diarylalkane Compounds via Binol-Catalyzed Conjugate Addition
A BINOL-catalyzed conjugate addition was shown in our laboratory to be compatible with unprotected indole substrates. This was considered to be an advantage over typical organometallic strategies since it allowed the use of mild boron-based nucleophiles. With this well established method, we …
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Development and Mechanistic Investigation of Indium(III)-Catalysed Hydrosilane Reduction of Imines
… complexes of In(III) and various functionalised BINOL ligands or BINOL derivatives have been investigated as catalysts for the hydrosilane reduction of imines. The functionalised BINOL ligands employed include a range of C1-symmetric BINOL ligands, which were synthesised as part of a project on …
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Harnessing cheminformatics for catalyst design I. Investigation into a general, asymmetric synthesis of cinchona alkaloid analogs towards asymmetric phase transfer II. Development of an enantioselective brønsted acid catalyzed four-component Ugi reaction
… catalyzed cyclopropanation reaction. Second, (R)-BINOL derived phosphoric acids were studied in regards to the brønsted acid catalyzed Ugi reaction. In regards to Cinchona alkaloids, the concentration was first on methodology develop to rapidly synthesize diverse Cinchona-like analogs in a highly …
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Asymmetric syntheses of anthraquinonyl C-glycosides
… employing the chiral titanium complexes Ti[(R)-BINOL]C12, Ti[(R)-BINOL]2, and Ti[R,R)-TADDOL]C12 were investigated. No reaction was observed when 0.5, 1.2 and 2 equivalents of Ti[(R)-BINOL]2 were used. However the complexes Ti[(R)-BINOL]C12 and Ti[(R,R)-TADDOL]C12 promoted the reaction between …
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Development of Improved Methodologies Toward the Formation of C-C and C-N Bonds
… method for the synthesis of 3,3'-bis-arylated BINOL derivatives through an ortho C-H borylation of commercially available (R)-BINOL followed by an in situ Suzuki-Miyarua coupling. Conventionally, these compounds are made via time-consuming multi-step routes. Development of this new method, …
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Asymmetric Catalysis with Brønsted Acids: Experiments and Calculations
… focuses on enantioselective catalysis using BINOL-based Brønsted acids. The initial part of this work comprises the development of chiral phosphoric acids and N-triflylphosphoramides having alternative groups at the 3,3’- positions, different from the widely common aryl scaffolds. These …
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I. Palladium-catalyzed anti-Markovnikov oxidative amination of olefins II. Catalytic deracemization of axially chiral diols III. Three component carboamination of electron deficient alkenes
… shown a copper-catalyzed deracemization of 2,2’-BINOL. Discovery of a catalyst capable of racemizing BINOL under mild conditions, combined with a resolving agent such as a cinchonidinium salt capable of sequestering a single desired enantiomer, creates a system that can convert any enantiomeric …
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Beiträge zur Synthese von Modellsystemen des heterobicyclischen Grundgerüstes der Saragossasäuren/Squalestatine sowie methodische Untersuchungen zur chemoselektiven mono-Debenzylierung von N,N-Dibenzylaminen und katalytischen enantioselektiven Ringöffnung von meso-Epoxiden
… Heterobimetall-Katalysatoren auf Basis von BINOL-Liganden entwickelt. Diese Katalysatoren wurden für die asymmetrische Ringöffnung verschiedener meso-Epoxide mit 4-Methoxyphenol genutzt und lieferten die Öffnungsprodukte in guten Ausbeuten und Enantiomerenüberschüssen (ee: 80 - 90 %).
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Design and synthesis of components for optically active metal-organic frameworks (MOFs) and synthetic routes to diverse deuterium labelled α-diazoacetates, α-diazoacetamides, α-diazoketones, and the antibiotic azaserine
… a selection of novel axially chiral (S)-BINOL-derived building blocks bearing 1,2,3-triazole moieties is described. Secondary functional groups can undergo post-synthetic modification resulting in the introduction of a catalytically active site. Within this research project an effective …
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Quantenchemische Berechnungen zur enantioselektiv katalysierten Aldolreaktion
… So wurde der gesamte katalytische Cyclus der Ti-BINOL katalysierten Reaktion berechnet, wobei sich der Einsatz der DFTB-Methode (density-functional based tight-binding method) zur Berechnung des Systems als sehr gut geeignet erwies. Die Leistungsfähigkeit der DFTB Methode konnte im Vergleich mit …
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Synthesis of the Antimalarial Flindersial Alkaloids
… a 2-enone tryptamine in the presence of base. A BINOL catalyzed enantioselective conjugate addition of a vinyl boronic acid to the 2-enone tryptamine has been achieved. A pyrrolo[a]indole unit could be connected to another indole unit by a Sonagashira coupling reaction in a convergent manner.
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Brønsted Acid Catalyzed Carbon-Carbon Bond Forming Reactions
… rearrangement afforded desired mono-protic BINOL based sulfonic acid was successfully performed. This will be followed by evaluating sulfonic acid catalytic efficiencies towards asymmetric coupling reactions.</p> <p>The total synthesis of latifolian A through application of a chiral sulfonic …
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Studies towards the Organocatalytic ‘Dialled In’ Synthesis of Chiral, Non-Racemic Aziridines, and Amino Acids, Containing Multiple Isotopic Labels
… C2 symmetric 3,3’- anthracenyl functionalised BINOL triflylphosphoramide organocatalyst, which allows for the formation of the desired cis- N-aryl 3-aryl-aziridine-2-carboxylates in an effective and highly enantioselective manner (affording the desired materials in yields of up to 81 %, and …
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Towards polyethylene-based materials with non-alternatively incorporated carbon monoxide monomer
… nickel(II) dimethyl) with either a BINOL (1,1′-bi-2-naphthol)-based phosphine diphenol (P,O) ligand or an analogous ligand which features an ethyl ether in place of the nonortho phenol. All complexes were active for ethylene homopolymerization (featuring activity up to 81.3 × 105 g …
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Retro-Diels-Alder routes to 4,5 disubstituted cyclopentenones
… ligands containing the diol functionality namely BINOL and the TADDOLs.
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HARNESSING NATURE’S MACHINERY: CHARACTERIZATION OF BACTERIAL BIOSYNTHETIC ENZYMES FOR CHALLENGES IN ORGANIC SYNTHESIS
… biaryl compounds like 1,1'-bi-2-naphthol (BINOL). Finally, in Chapter 6, we report the first in vitro characterization of Mas10, a putative amide synthase proposed to forge the 13-membered macrolactam in the biosynthesis of the microansamycins. Here, we demonstrate the selectivity for …
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The Synthesis and Application of a Chiral Sulfonated Phosphine Ligand to Asymmetric Transition-Metal Catalysis
… of a linear chemical resolution route, using (R)-BINOL as a chiral auxiliary, is described. This route allows access to sSPhos in its enantiopure form. The enantiopure sSPhos was then investigated as a chiral ligand in the fields of palladium and gold chemistry. sSPhos was evaluated as a chiral …
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Organocatalytic synthesis of chiral non-racemic aziridines, labelled with 2H, 15N, 13C stable isotopes
… 13C and 15N. The reactions were catalysed by (S)-BINOL derived N-triflylphosphoramide Brønsted acid and stable isotopes were selectively introduced within an aziridine ring with > 95% isotopic enrichment. The desired compounds were generated in yields of up to 81% and up to 87% e.e. Furthermore …
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Structure-Property Relationship of the Two-Photon Circular Dichroism of Compounds with Axial and Helical Chirality
… of a full TPCD spectrum was performed on BINOL enantiomers and the results were supported and discussed with the help of theoretical calculations. After that seminal work, we embarked in expanding the understanding of the structure-property relationship of TPCD by performing, …
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Exploring Enantioselective and Multicomponent One-Pot Reactions Utilizing Alkynes as Linchpins Toward Biologically Active Molecules
… functionalized dienes. Herein we report a new BINOL-Al-Cl catalyst preparation that is robust enough to catalyze such a reaction with great success both in terms of yield and enantiomeric ratios. The products, 1,4-cyclohexadienes, have two regiochemically different alkenes, which can serve as …
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