Дисертації з теми "Enaminone synthesis"
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Ostric, Adrian. "Hydroxyethylene isosters of Xaa-Pro dipeptides: synthetic approaches and new HIV-PR inhibitors." Doctoral thesis, Università degli studi di Trieste, 2011. http://hdl.handle.net/10077/4576.
Повний текст джерелаThe aspartic protease (HIV-Pr) of the human immunodeficiency virus, responsible agent for AIDS, is surely one of the most studied enzymes in terms of structure and activity. HIV-Pr is responsible for cleaving the viral polyprotein precursor into structural proteins and enzymes and plays an essential role in the viral replication and maturation. HIV-Pr has thus become the target of numerous efforts to design antiviral therapeutic agents suitable for the treatment of AIDS. In the field of organic chemistry, the search for effective HIV-Pr inhibitors has boosted the development of new methodologies for the stereoselective synthesis of compounds containing multiple chiral centers, on which reversible inhibitors are generally based. HIV-Pr shows peculiar characteristics as it is able, unlike any other eukaryotic aspartic protease, to hydrolyze amide bonds with proline as the N-terminal residue. Moreover, it is active in a dimeric form, possessing C2 symmetry, in which each monomer contributes a catalytic aspartate. The first part of the present doctoral work described in Chapter 2, has been dedicated to the synthesis of hydroxyethylene Phe-Pro isosters in which the pyrrolidine ring is expanded by a condensed aromatic ring in order to provide a better fit to the enzyme’s catalytic site. During the synthesis of the isoster a novel reaction was discovered in which enaminones are directly formed by treatment of α,β-unsaturated ketones with trimethylsilylazide and fluoride. Phe-Pro isosters based on the enaminone structure showed moderate activity as HIV-Pr inhibitors. The direct amination of α,β-unsaturated ketones is the subject of Chapter 3. This reaction is demonstrated to be general for enones containing a β-hydrogen. A mechanism based on azide activation via formation of a pentacoordinated silicon species followed by a 1,3-dipolar cycloaddition is proposed and supported by experimental results and calculations. In Chapter 4 is reported the synthesis of a library of triazole inhibitors by a combinatorial approach based on click chemistry. The library was screened for HIV-Pr inhibition and deconvoluted. A set of promising members from the library was synthesized as single, enantiomerically pure compounds that confirmed to be active HIV-Pr inhibitors. Finally, in Chapter 5 the development of an alternative approach to dipeptide isosters, based on the ring closing metathesis of aminoacid-derived allylamines, is described. Building of the four carbon atom backbone of the isosteres is obtained after mounting the olefins on designed linkers that allow selectivity in the cross metathesis, and easy final cleavage. Carbamate linkers will also allow also protection of the amino groups during the next steps of the synthesis leading to the desired di- and monohydroxyethylene isosters.
La proteasi aspartica (HIV-PR) del virus della immunodeficienza umana, l'agente responsabile dell'AIDS, è sicuramente uno degli enzimi più studiati in termini di struttura e di attività. HIV-Pr è responsabile della scissione della poliproteina virale in proteine strutturali ed enzimi e svolge un ruolo essenziale nella replicazione e maturazione del virus. HIV-Pr è così diventato il bersaglio di numerosi studi mirati alla progettazione di agenti terapeutici antivirali adatti per il trattamento dell'AIDS. Nel campo della chimica organica, la ricerca di efficaci inibitori dell'HIV-Pr ha stimolato lo sviluppo di nuove metodologie per la sintesi stereoselettiva di composti contenenti più centri chirali, che costituiscono la base strutturale della maggior parte degli inibitori reversibili. HIV-Pr presenta caratteristiche peculiari in quanto è in grado, unica tra le proteasi aspartiche da eucarioti, di idrolizzare legami ammidici con la prolina come residuo N-terminale. Inoltre, l’enzima è attivo in una forma dimerica, con simmetria C2, in cui ogni monomero contribuisce con un residuo catalitico di acido aspartico. La prima parte del presente lavoro di dottorato, descritta nel capitolo 2, è stata dedicata alla sintesi di isosteri idrossietilenici del dipeptide Phe-Pro, contenenti un anello pirrolidinico espanso al fine di migliorare le interazioni con il sito catalitico dell'enzima. Durante la sintesi dell’ isostere è stata scoperta una nuova reazione di formazione di enaminoni per trattamento di chetoni α,β-insaturi con trimethylsilylazide e fluoruro. Alcuni isosteri Phe-Pro basati sulla struttura enaminonica hanno mostrato una moderata attività come inibitori della HIV-PR. L'amminazione diretta di chetoni -insaturi è il soggetto del capitolo 3. Questa reazione si è dimostrata essere generale per enoni contenente un idrogeno in posizione β. Un meccanismo basato sulla attivazione della azide attraverso la formazione di una specie pentacoordinata di silicio seguita da una cicloaddizione 1,3-dipolare viene proposto sulla base dei risultati sperimentali e di calcoli teorici. Nel capitolo 4 è riportata la sintesi di una libreria di inibitori triazolici ottenuti con un approccio combinatoriale. La libreria è stato analizzata per l'inibizione di HIV-Pr e deconvoluta. Alcuni membri promettenti della biblioteca sono stati sintetizzati come composti singoli, in forma enantiomericamente pura, confermandosi attivi inibitori della HIV-PR. Infine, nel capitolo 5, é descritto lo sviluppo di un approccio alternativo a isosteri di dipeptidi, basato sulla “ring closing methatesis” di allilamine derivate da aminoacidi. La costruzione dello scheletro degli isosteres si ottiene dopo l’assemblaggio delle olefine su un nuovo linker che consente una cross-metatesi selettività nonché un facile distacco del prodotto. Il linker può anche essere utilizzato come gruppo proteggente nella successiva elaborazione sintetica dei prodotti.
XXIII Ciclo
1981
Sinibaldi, Marie-Eve. "Nouveaux intermediaires pour la synthese d'alcaloides pentacycliques : synthese totale de la desethyl-20 acetyl-20 aspidospermidine." Clermont-Ferrand 2, 1988. http://www.theses.fr/1988CLF21144.
Повний текст джерелаPereira, Fernando Luiz Cardoso. "Aplicações sintéticas de β-enamino ésteres." Universidade de São Paulo, 2002. http://www.teses.usp.br/teses/disponiveis/46/46135/tde-19112015-162222/.
Повний текст джерелаA series of acyclic β-enamino esters was submitted to iodocyclization reactions or to iodine-mediated lactonization, leading to the corresponding cyclic iodo-β-enamino esters or β-enamino lactones. Dehydroiodination of the five-membered ring enamino esters furnished pyrrole, tetrahydroindole and hexahydroindole derivatives, under basic or neutral conditions. The six-membered ring enamino esters, when submitled to treatment with triethylamine, gave rise to trisubstituted cyclopentanes. This transformation occurred through an intramolecular nucleophilic substitution, instead of the expected dehydroiodination reaction. The effect of the N-substituent in these reactions was studied for a series for N-alkyl and N-aryl derivatives. The β-enamino lactones were obtained in poor yields, due to the poliiodination of the substrates, and showed to be resistent to reduction of the carbon-carbon double bond under several conditions. A study of conformational analysis of the bicyclic β-enamino esters was undertaken, using 1H-NMR and13C-NMR data, molecular mechanics and semi-empirical methods. From this study, it was observed that the bicyclic compounds adopt different conformations depending upon the N-substituent.
González, Soria María José. "Selective synthesis and reactivity of indolizines." Doctoral thesis, Universidad de Alicante, 2018. http://hdl.handle.net/10045/98672.
Повний текст джерелаThroup, Adam Eric. "Synthetic methodology and application of enamine [2+2] cyclisations for cyclobutane synthesis : development of integrin antagonists as anticancer therapeutics towards a total synthesis of providencin." Thesis, University of Bradford, 2015. http://hdl.handle.net/10454/14411.
Повний текст джерелаThroup, Adam E. "Synthetic Methodology and Application of Enamine [2+2] Cyclisations for Cyclobutane Synthesis. Development of Integrin Antagonists as Anticancer Therapeutics Towards a Total Synthesis of Providencin." Thesis, University of Bradford, 2015. http://hdl.handle.net/10454/14411.
Повний текст джерелаDELBECQ, PHILIPPE. "Nouvelles voies d'acces aux beta-enaminones cycliques. Application a la synthese de la six-methylpelletierine." Paris 6, 1990. http://www.theses.fr/1990PA066472.
Повний текст джерелаSevenich, Adrian Manuel [Verfasser]. "Entwicklung und Anwendung photochemischer Reaktionen zur Synthese und Modifikation von Heterocyclen : Synthese von (−)-Hexahydrofurofuranol; Synthese und Funktionalisierung von Enaminonen / Adrian Manuel Sevenich." Mainz : Universitätsbibliothek der Johannes Gutenberg-Universität Mainz, 2021. http://d-nb.info/122704853X/34.
Повний текст джерелаTaylor, Jane M. "The design and synthesis of acylated enamino esters as potential inhibitors of serine proteases." Thesis, University of Canterbury. Chemistry, 1993. http://hdl.handle.net/10092/8000.
Повний текст джерелаDeng, Yongming. "Asymmetric cyclization reactions through an enamine/acid cooperative approach. Synthesis of unsymmetrically functionalized benzoporphyrins." Miami University / OhioLINK, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=miami1406213121.
Повний текст джерелаLallemand, Marie-Christine. "Etude de la réactivité de la 2-cyano-6-phényloxazolopipéridine et de ses dérivés 2-alkyles précurseurs d'énamines." Paris 11, 1996. http://www.theses.fr/1996PA114806.
Повний текст джерелаZhao, Qiang. "Development of New Synthetic Transformations of N-Sulfony1-1,2,3-triazoles." Kyoto University, 2019. http://hdl.handle.net/2433/242534.
Повний текст джерелаDAKA, PHILIAS. "ENAMINE-METAL LEWIS ACID BIFUNCTIONAL CATALYSTS FOR ASYMMETRIC ALDOL REACTIONS. DESIGN AND SYNTHESIS OF STAT3 INHIBITORS." Miami University / OhioLINK, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=miami1374852476.
Повний текст джерелаDePizzo, Ashley. "Synthesis of bis(2,2,2-trifluoroethyl) β-ketophosphonates from bis(2,2,2-trifluoroethyl) 1-alkynylphosphonates via enamine vinyl phosphonates". Youngstown State University / OhioLINK, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1287586787.
Повний текст джерелаLACROIX, ERIC. "Syntheses cyclopropeniques de polyquinanes." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13123.
Повний текст джерелаDohe, Janis [Verfasser], Thomas J. J. [Akademischer Betreuer] Müller, and Klaus [Gutachter] Schaper. "Synthese von festkörperlumineszenten Bordifluorid Enaminon Komplexen auf Basis einer Palladium-katalysierten Multikomponentenreaktion / Janis Dohe ; Gutachter: Klaus Schaper ; Betreuer: Thomas J. J. Müller." Düsseldorf : Universitäts- und Landesbibliothek der Heinrich-Heine-Universität Düsseldorf, 2018. http://d-nb.info/1150477466/34.
Повний текст джерелаZhang, Yang. "Dynamic Systems : Enzymatic Synthesis, Exchange Reactions and Applications in Materials Science." Doctoral thesis, KTH, Organisk kemi, 2015. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-173480.
Повний текст джерелаQC 20150911
Charlton, Andrew. "Towards the development of direct methodology to enantioenriched α-alkylated aldehydes". Thesis, University of Oxford, 2013. http://ora.ox.ac.uk/objects/uuid:bcfe43bb-1497-4f94-bcc7-6f7c2ae0b3a1.
Повний текст джерелаHAMMAMI, HEDI. "Reaction de beta-enamino esters chiraux avec les olefines electrophiles : synthese asymetrique de beta-ceto esters alpha, alpha-disubstitues, applications synthetiques." Paris 6, 1993. http://www.theses.fr/1993PA066380.
Повний текст джерелаWürtz, Sebastian. "Palladium-Katalyse Synthese und Anwendung neuartiger chiraler und achiraler N-heterocyclischer Carbene (NHC) in Palladium-katalysierten Kreuzkupplungen und Palladium-katalysierte oxidative Cyclisierung von N-Aryl-Enaminen zur Synthese hochfunktionalisierter Indole." Lichtenberg (Odw.) Harland Media, 2008. http://d-nb.info/992466458/04.
Повний текст джерелаXie, Sheng. "Perfluroaryl azides : Reactivities, Unique Reactions and their Applications in the Synthesis of Theranostic Agents." Doctoral thesis, KTH, Organisk kemi, 2015. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-172950.
Повний текст джерелаQC 20150903
Léger, Frédéric. "Additions d'énamines β-lithiées sur des esters α, β-éthyléniques. Nouvelles propriétés des énamines β-halogénées". Rouen, 1996. http://www.theses.fr/1996ROUES051.
Повний текст джерелаBarth, Francis. "Synthese de squelettes mono et sesquiterpeniques au depart de cyclopropenes et cyclobutenes electrophiles." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13167.
Повний текст джерелаCUSSERNE, BARDOU ANITA. "Etude de la reduction et de l'alkylation des -enamino esters cycliques. Application a la synthese hautement enantioselective de trois alcaloides de venins d'amphibiens : les (-) (5r, 8r, 8as) indolizidines 181b, 209b et 223i." Paris 6, 1997. http://www.theses.fr/1997PA066293.
Повний текст джерелаAl, Badri Hashim. "Synthèse et réactivité d'énamines phosphoniques fonctionnelles et de phosphonates allyliques. Applications à la synthèse de diènes fonctionnels utilisés dans la réaction de Diels-Alder." Rouen, 1996. http://www.theses.fr/1996ROUES054.
Повний текст джерелаLéon, Patrick. "Alkylation d'amines par les sels de sulfonium, reaction de type gabriel et synthese de polyamines." Paris 6, 1987. http://www.theses.fr/1987PA066488.
Повний текст джерелаPuchot, Catherine. "Contribution à l'étude des synthèses asymétriques catalysées par les acides aminés." Paris 6, 1986. http://www.theses.fr/1986PA066136.
Повний текст джерелаMarabout, Benoît. "Synthèse totale de la ( + ou - ) perhydrohistrionicotoxine." Rouen, 1988. http://www.theses.fr/1988ROUES019.
Повний текст джерелаScalzullo, Stefania Margherita. "Synthesis of lamellarin alkaloid analogues from enaminone precursors." Thesis, 2014.
Знайти повний текст джерелаSultan, Saleem Syed. "The synthesis of 8-substituted indolizidines from enaminone precursors." Thesis, 2012. http://hdl.handle.net/10539/11615.
Повний текст джерелаRiley, Darren Lyall. "Synthesis of amphibean indolizidine alkaloids and related compounds from enaminone precursors." Thesis, 2008. http://hdl.handle.net/10539/4967.
Повний текст джерелаMthembu, Siyanda Thabani. "Enaminone-based approaches to the synthesis of alkaloids possessing the pyrrolo[1,2-a]azepine core." Thesis, 2018. https://hdl.handle.net/10539/26053.
Повний текст джерелаThis thesis illustrate strides taken toward the construction of the pyrrolo[1,2-a]azepine 4 nucleus via enaminone chemistry developed in this University for creating pyrrolizidine 1, indolizidine 2 and quinolizidine 3 alkaloids. The pyrrolo[1,2-a]azepine 4 core is a fused pyrrolidine and azepine system found in lehmizidine, Stemona, Cephalotaxus alkaloids and other alkaloids. A concise background is given on the nature of enaminones, how they are accessed with strong emphasis on the Eschenmoser sulphide contraction reaction and their versatile reactivity, followed by literature review of this University background on synthesis of alkaloids containing 1, 2 and 3 nuclei. The aims and strategies presented are preceded by literature review of lehmizidine, Stemona, Cephalotaxus alkaloids and some reported synthesis. A range of attempts and successes are reported in chapter 2 for making four-carbon chain length enaminones (via N-alkylation, condensation, thionation, Eschenmoser sulphide contraction and tandem acylation/Michael addition reactions) crucial in creating azepane onto pyrrolidine in an acylation or alkylation ring closing steps yielding lehmizidine like compounds (E)-ethyl 8-oxo- 2,3,5,6,7,8-hexahydro-1H-pyrrolo[1,2-a]azepine-9-carboxylate 144 and (E)-ethyl 2,3,5,6,7,8- hexahydro-1H-pyrrolo[1,2-a]azepine-9-carboxylate 147. Vice versa, the synthesis of two carbon chain length N-alkyl vinylogous amides is demonstrated leading to the formation of pyrroles, ethyl 2-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-3-carboxylate 222, ethyl 2-(4-nitrophenyl)- 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-3-carboxylate 223 and ethyl 2-(4-methoxyphenyl)- 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-3-carboxylate 224 in Knoevenagel condensation reactions similar to those described by Garreth Morgans and Stefania Scalzullo in their PhD theses. The synthesis of 1-benzoyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-2,3-dione 233 and 1-(4-methoxybenzoyl)-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-2,3-dione 235 in a double acylation reaction between NH vinylogous amides and oxalyl chloride is also demonstrated. In chapter 3, the synthesis of vinylogous urethanes for making the Cephalotaxus core via Nalkylation, condensation, thionation, Eschenmoser sulphide contraction and tandem acylation/Michael addition reactions are described. A variety of attempts of the arylation reaction on vinylogous urethanes are demonstrated leading to a comparison study to ascertain carbon chain length dependency of the step. The synthesis of pyrido[1,2-a]azonine nucleus of Sessilifoliamide alkaloids, which are a subset of the Stemona alkaloids demonstrated in chapter 4 is in line with our fascination with bigger ringed alkaloids. The synthetic route is presented leading the formation of compounds 1-benzoyl-3- methyl-2,3,7,8,9,10,11,12-octahydropyrido[1,2-a]azonin-4(6H)-one 337, 3-methyl-1-(4- nitrobenzoyl)-2,3,7,8,9,10,11,12-octahydropyrido[1,2-a]azonin-4(6H)-one 338 and 1-(4- methoxybenzoyl)-3-methyl-2,3,7,8,9,10,11,12-octahydropyrido[1,2-a]azonin-4(6H)-one 339.
LG2018
Mthembu, Siyanda Thabani. "Enaminones in the synthesis of azabicyclic models for alkaloids." Thesis, 2008. http://hdl.handle.net/10539/5725.
Повний текст джерелаMorgans, Garreth Llewellyn. "New routes to arylated azabicyclic systems from enaminones, and applications to alkaloid synthesis." Thesis, 2009. http://hdl.handle.net/10539/6887.
Повний текст джерелаThroup, Adam, Laurence H. Patterson, and Helen M. Sheldrake. "Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones." 2016. http://hdl.handle.net/10454/9488.
Повний текст джерелаFused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.
The work was funded by Yorkshire Cancer Research
Zheng-YanLu and 呂政彥. "Synthesis of Quinolines from Enamine Derivatives via Copper-catalyzed Oxidation Reaction." Thesis, 2014. http://ndltd.ncl.edu.tw/handle/9stfk2.
Повний текст джерела國立成功大學
化學系
102
In organic synthesis, transition metals as the catalysts have been widely using in industrial or research purpose. Using copper salts as a catalyst compared with other transition metal salts (Ex. Pd(II)、Pd(IV)、Au(III) or Ag(II)), copper salts have relatively inexpensive and environmental friendly characters, etc. Also, copper catalysts in the radical oxidation reaction are great tool for forming the carbon-carbon bond, therefore, The thesis is focus on this study.
Lin, Pin-Chun, та 林品君. "Double Michael Addition in the synthesis of α-2-Deoxy-Ulosides from β-enamino Ketone". Thesis, 2012. http://ndltd.ncl.edu.tw/handle/92471348350965285743.
Повний текст джерела中國醫藥大學
藥物化學研究所碩士班
101
Hex-1-en-3-one that had been prepared by oxidation reactions of D-glucals or D-galactals were subjected to Michael addition15 with 3.0 equiv of primary amines (including benzylamine, n-butylamine, and n-octylamine) in MeOH for 2 h. The products,β-Enamino ketone 26, were obtained in 87-95% with high diastereoselective Z-geometry due to the intramolecular hydrogen bonding. β-Enamino kentone 26a reacted with n-hexanol under basic conditions. Several Lewis acids (3.0 equiv), solvents and temperatures were examined. Among these reaction shown that 12N HCl (3.0 equiv) at 100 W/60 oC for 10 min was found to provide the desired product n-hexyl-2-deoxy-α-deoxyulosides (27) with the highest isolated yield (88%) and stereoselectivity (ratio of α/β-amomers: 95/5). α-2-Deoxyglycosides were synthesized in good yields by microware-assisted reaction of β-enamino ketone with various O- and S-nucleophiles in the presence of 3.0 equiv of hydrogen chloride. These glycosyl additions were throgh the double Michael reaction and occurred high α-stereoselectivity and were complete in 10 min in 51-93% yield. The palladium complex were synthesized in good yields by reacting β-enamino ketone with palladium(II) acetate in the presence of 5.0 equiv of sodium bicarbonate and 1.0 equiv of tetrabutylamino bromide in DMF at room temperature for 3 h.
Pei-JuTsai and 蔡佩如. "Synthesis of Quinolines by Manganese(III) Acetate Mediated Oxidative Free Radical Reaction of Enamine Derivatives." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/15704327191823358554.
Повний текст джерела國立成功大學
化學系碩博士班
101
Free radical reactions have been recognized as a great tool for forming carbon-carbon bond in organic chemistry; especially the free radical cyclizations of alkenes to become polycyclic compounds. But the reactions are usually terminated by hydrogen atom transfer. In recent decades, oxidative free radical reactions with transition metal salts (Mn(III), Ce(IV), Ag(II) and Pb(IV) etc.) have been taken serious. Because the reactions are terminated by oxidation of the free radical to a carbocation, that can become various products. This thesis is divided into three parts: (1)Quinolines can be synthesized by the oxidative free radical reaction of N-(2’-stilbenyl)enamine derivatives with excess manganese(III) acetate under oxygen. (2)The oxidative free radical reaction of N-(2’-stilbenyl)enamine derivatives with catalytic amount manganese(III) acetate, excess cobalt(II) acetate and oxygen produce quinolines. (3)4-Acylquinolines can be synthesized by the oxidative free radical reaction of ethyl 3-(2-alkynylaniline)-3-benzylacrylate derivatives with excess manganese(III) acetate under oxygen and catalytic manganese(III) acetate combined with excess cobalt(II) acetate and oxygen respectively.
Arend, Michael. "Regio- und stereoselektive Synthese von Mannich-Basen durch Addition von Enaminen und Iminen an Iminiumsalze /." 1996. http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&doc_number=007410505&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA.
Повний текст джерелаTsai, Chia-Chung, та 蔡嘉忠. "一、New, Simple, and Practical Enamine Cyclopropanation Using CH2Cl2二、TiCl4-Mg Promoted Direct Coupling of CHCl3 to Aldehydes, Ketones, and Enamines.三、Asymmetric Synthesis of (+)-Valienamine". Thesis, 2007. http://ndltd.ncl.edu.tw/handle/40513439465041150540.
Повний текст джерела中興大學
化學系所
95
一、New, Simple, and Practical Enamine Cyclopropanation Using CH2Cl2 Abstract: Dichloromethane serves as a novel electrophilic carbene equivalent which adds to an enamine double bond. The presence of other alkenes moieties in the enamine partner is well tolerated. Even enamines derived from sterically hindered ketones react readily with dichloromethane promoted by TiCl4-Mg. 二、TiCl4-Mg Promoted Direct Coupling of CHCl3 to Aldehydes, Ketones, and Enamines. Abstract: Direct oxidative addition of CHCl3 to the Mg-TiCl4 bimetallic species resulted in the generation of an ambiphilic chloromethylenetitanium complex, which not only effected nucleophilic addition to aldehydes and ketones to provide vinyl chlorides but also served as an electrophilic carbene complex to effect enamine-cyclopropanation to give chlorocyclopropanes. 三、Asymmetric Synthesis of (+)-Valienamine Abstract: (+)-valienamine, a potent glycosidase, has a cyclohexene framework containing one amino and three hydroxyl groups on four stereogenic carbons. A new strategy toward enantiopure O-isopropylidene-protected valienamine evolved from controlled construction of a C2 chiral O-isopropylidene-protected cyclohexenediol via ruthenium-catalyzed ring closing metathesis of a C2 chiral O-isopropylidene-protected octadienediol. Regiocontrolled introduction of the hydroxymethyl unit via palladium-promoted carbonylation of vinyl triflate followed by stereocontrolled installation of the amino unit via a displacement of hydroxyl group with net inversion of configuration led efficiently to isopropylidene-protected valienamine. The requisite C2 chiral octadienediol was readily prepared from the (+)-tartaric acid via a three-step protocol: (a) conventional one-pot elaboration of tartaric acid into O-isopropylidene-protected diamide, (b) coupling of diamide with vinylmagnesium bromide, and (c) stereocontrolled reduction of dienedione. The total asymmetric synthesis of O-isopropylidene-protected valienamine was thus realized in fourteen steps with an overall yield of 10.5%. The present route also indicates several shortcomings of current methodology that, once resolved, will provide further efficiency of this route to (+)-valienamine.
Limbach, Michael. "Ein Baukastensystem zum universellen Aufbau kleiner rigidifizierter Peptidomimetika und spirocyclopropanierter Wirkstoffanaloga." Doctoral thesis, 2004. http://hdl.handle.net/11858/00-1735-0000-0006-B0C3-0.
Повний текст джерелаKlapa, Katharina Anna. "Untersuchungen zur Synthese von Yohimban- und Campthoteca-Alkaloiden durch Domino-Knoevenagel-Hetero-Diels-Alder-Reaktion." Doctoral thesis, 2007. http://hdl.handle.net/11858/00-1735-0000-0006-AC9C-5.
Повний текст джерелаWu, Yao-Ting. "β-Aminosubstituted α,β-Unsaturated Fischer Carbene Complexes as Precursors for Complex Oligocyclic Molecules - Basics and Applications". Doctoral thesis, 2003. http://hdl.handle.net/11858/00-1735-0000-0006-B61B-7.
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