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Dissertations / Theses on the topic 'Asymmetric synthesis'

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Published: 4 June 2021

Last updated: 25 July 2025

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1

Case-Green, S. C. "Double asymmetric synthesis." Thesis, University of Oxford, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.293361.

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2

Ridge, Katerina. "Absolute asymmetric synthesis." Thesis, University of Surrey, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.493053.

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One possible way of achieving absolute asymmetric synthesis is by "freezing" the chirality of a molecule by crystaUisation. This work is a study of the synthesis of :ertain imides which have potential for axial chirality and are likely to undergo spontaneous resolution on crystallisation. The synthesis starts from achiral compounds and therefore, if it does yield chiral crystals by spontaneous resolution, it can be classified as absolute asymmetric synthesis.

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3

Lewis, Neil. "Asymmetric piperidine synthesis." Thesis, University of Nottingham, 1995. http://eprints.nottingham.ac.uk/13293/.

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It has been demonstrated that bakers' yeast reduction of 1-tert-butyl-2-methyl 3-oxo-piperidine-1,2-dicarboxylate gives (2R, 3S), 1-tert-butyl-2-methyl 3-hydroxy-piperidine-1,2-dicarboxylate in 80% chemical yield with >99% d.e. and >97% e.e. Also bakers' yeast reduction of 1-tert-butyl-3-ethyl 4-oxo-piperidine-1,3-dicarboxylate gives (3R, 4S), 1-tert-butyl-3-ethyl4-hydroxy-piperidine-1,3-dicarboxylate in 74% chemical yield with >99% d.e. and >93% e.e. The optical purity and absolute configurations of the hydroxy-ester derivatives were determined by conversion into the corresponding chiral bis-

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4

Pedersen, Daniel Sejer. "Asymmetric cyclopropane synthesis." Thesis, University of Cambridge, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.613762.

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5

Harris, Matthew Eben. "Asymmetric lactam synthesis." Thesis, University of Warwick, 2013. http://wrap.warwick.ac.uk/58635/.

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Broad-Spectrum Chemokine Inhibitors (BSCIs) are a novel type of antiinflammatory drug, discovered by Fox and colleagues. We have shown that the syntheses of C-substituted γ-thialactams are possible via a modular approach starting from the simple amino acid cystine. These compounds are a new class of GPCR ligand, showing BSCI activity comparable to their non-sulfur counterparts. Initial migratory data suggests that these lactams are inhibitors of leukocyte migration and comparable to the analogous BSCI lactams at μM concentrations, with decreased activity at the nM scale. Efforts have been made

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6

Ravindran, Swarnam Shanthi. "Studies in asymmetric synthesis." Thesis, Rhodes University, 1994. http://hdl.handle.net/10962/d1005017.

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The stereoselectivity of TiCI₄-catalysed Mukaiyama reactions of a camphor acetal-derived chiral silyl enol ether with a range of substituted aromatic aldehydes has been examined. The enantiomeric excess in each of the resulting ß-hydroxy ketones, determined by ¹H NMR spectroscopy using the lanthanide chiral shift reagent Pr(Etcf₃), ranged between 9 and 13%. The stereo-directing potential of the camphor acetal as a chiral auxiliary in the α-benzylation of carboxylate esters has been studied; the acids were chosen to illustrate substituent effects on asymmetric induction. The observed diastereos

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7

Wang, Ziyu, та 汪子玉. "Organocatalytic asymmetric synthesis of dihydrodibenzofurans and asymmetric aziridination of α-nitroalkenes". Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2012. http://hdl.handle.net/10722/193388.

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The synthesis of useful chiral skeletons from simple achiral starting materials is always the dream of organic chemists. In the past decades, organocatalysis has been rapidly developed and has become one of the most important methods in asymmetric catalysis. The aim of this thesis is to develop asymmetric methods for the construction of useful chiral skeletons based on organocatalytic chemistry. Many natural products and biologically important compounds contain the hydrogenated dibenzofuran (Figure 1) as a common sub-structure. In the first part of this thesis, the first amine-catalysed asymm

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8

White, Rachael A. "Asymmetric Synthesis of Prostaglandins." Digital WPI, 2005. https://digitalcommons.wpi.edu/etd-theses/735.

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Prostaglandins (PGs) are medicinally interesting because of the wide variety of roles they play in the body. PGs are ubiquitous and can be found in the reproductive system, the nervous system, the cardiovascular system, and the immune system. Accordingly, PGs are an important therapeutic target for pharmaceutical companies, and an efficient synthesis is highly desirable. Past research indicates that an approach to prostaglandins via a chiral acetylenic ester or amide provides a promising method for control of C-15 geometry. This project seeks to validate a key stereospecific reduction of an en

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9

Ambler, P. W. "Asymmetric synthesis of cyclopropanes." Thesis, University of Oxford, 1988. https://ora.ox.ac.uk/objects/uuid:958e77c2-d15e-4d8f-af84-36dca36e4215.

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This thesis is concerned with the asymmetric synthesis of cyclopropyl derivatives via the use of chiral iron acyl complexes of the type (η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)Fe(CO)(PPh<sub>3</sub>)(COCH=CR'R), Chapter 1 reviews previous routes to optically active cyclopropyl derivatives and reviews the use of the chiral auxiliary (η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)Fe(CO)(PPh<sub>3</sub>) for asymmetric synthesis. Chapter 2 describes the synthesis of the complexes (η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)Fe(CO)(PPh<sub>3</sub>)(COCH=CRR') and presents a conformational an

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10

Dixon, Darren J. "Asymmetric synthesis of andrimid." Thesis, University of Oxford, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.337813.

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11

Santos, Soraia Patricia Pinto dos. "Asymmetric synthesis of Tetrahydropyrans." Thesis, University of York, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.489203.

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Tetrahydropyrans (THP) are important building blocks in organic synthesis, present in a variety of natural products with significant biological activity. The synthesis of these units has been achieved, first in a racemic manner where a one pot procedure was developed.

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12

Innes, J. F. "Dispiroketals in asymmetric synthesis." Thesis, University of Cambridge, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.604937.

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This thesis is divided into five Chapters. The first consists of an introduction to dispiroketals and an overview of what has been achieved through their application in organic synthesis. The second Chapter describes the use of (<I>2S,2'S</I>)-2,2'-diphenyl-6,6'-bi-3,4-dihydro-<I>2H</I>-pyran to achieve the asymmetric synthesis of (+)-D-conduritol B. The synthesis proceeds in nine steps from DL-1-<I>0,2-0:4-O,5-O-</I>dicyclohexylidene-<I>myo</I>-inositol and the key step is the simultaneous protection and resolution of a racemic diol <I>via </I>dispiroketal methodology. The optical rotation of

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13

Goddard, Euan. "Asymmetric Synthesis of Alkaloids." Thesis, University of Oxford, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.489446.

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14

Storer, N. P. "Asymmetric synthesis of lignans." Thesis, Swansea University, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.639120.

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An introduction to lignans, including classification, occurrrence, biological activity, the role of lignans and their biosynthesis, is described in chapter 1. Chapter 2 presents a review of the conjugate addition reaction, with particular emphasis on chiral conjugate additions. This chapter also reviews the synthesis of lignans <i>via</i> conjugate additions to both chiral and achiral acceptors. Chapter 3 describes an attempt to synthesize lignans <i>via</i> tandem conjugate additions to a chiral crotonate ester. The project was, however, unsuccessful, due to problems associated with the synth

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15

Sirit, A. "Asymmetric synthesis of butenolides." Thesis, Swansea University, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.639047.

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Optically active butenolides have been prepared from the reaction of chiral 1,3-dioxolans and 1,3-oxazolidines with the silyl enol ethers 2-trimethylsilyloxyfuran and 2-trimethylsilyoxy-4-methoxyfuran. Chiral 1,3-dioxolans were prepared in high yields (80-96%) by the exchange reaction of diisopropyl L-tartrate with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate. These were reacted with 2-trimethylsilyoxyfuran (TMSOF) under Lewis acid conditions to give optically active butenolides. The stereoselectivity and yield were not very good. (-)-(R)-Phenyl glycinol and (-)-(1R,

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16

Sparey, Tim. "Asymmetric synthesis using sulfimides." Thesis, University of Warwick, 1995. http://wrap.warwick.ac.uk/55816/.

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Asymmetric synthesis, the synthesis of chiral molecules, has developed into one of the most important areas of chemistry. Numerous methods are used to prepare chiral compounds, one of which involves using chiral acyl anion equivalents. The potential of imides of cyclic sulfimides 148 as chiral acyl anion equivalents was found to be limited to simple alkylations using sodium hydride and an alkyl iodide in DMF. Alkylated adducts 154,158 and 159 were prepared with good diastereoselectivity, with the anti and anti-anti geometries being preferred for 154 and 158, and 159, respectively. The conforma

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17

Simpson, Carol Jane. "Towards enzymatic asymmetric synthesis." Thesis, University of East Anglia, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.398495.

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18

Baird, Charlotte. "Sulfimide-mediated asymmetric synthesis." Thesis, University of Warwick, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.338708.

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19

Xu, Youli. "Asymmetric synthesis involving silicon." Thesis, Open University, 1996. http://oro.open.ac.uk/57654/.

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Several different types of optically active, synthetically useful, silylated diols (17 pairs) have been prepared by asymmetric dihydroxylation of the corresponding allyl and vinylsilanes using Sharpless catalysts. Chiral analysis of these silyl diols was carried out by 1H NMR methods in the presence of Eu(hfc)3. Enantiomeric purity of some of these silyl diols is greater than 90% e. e. Synthetically more useful, optically active trimethylsilylepoxides, trimethylsilyl amino alcohols and aziridines have been isolated by a multi-stage chirality transfer from their precursor diol involving no race

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20

Yoshizawa, Akina. "Azetidines for asymmetric synthesis." Thesis, University of Birmingham, 2018. http://etheses.bham.ac.uk//id/eprint/8719/.

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The creation of asymmetric ligands with lower environmental impact is important, as such chiral N,N' ligands attract some attention. A new method for the synthesis of 1,2,4-trisubstituted amino azetidines with \(cis\) relative configuration across its two stereogenic centres was reported in 2013. Due to this \(cis\) conformation, the azetidine compounds are expected to be good chiral ligands for asymmetric catalysis. The nitro aldol (Henry) reaction is an established method for producing new carbon-carbon bonds and is a key reaction in the synthesis of many important compounds. Enantioselectiv

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21

Reignier, Serge. "Sulfur in asymmetric synthesis." Thesis, Loughborough University, 2002. https://dspace.lboro.ac.uk/2134/33720.

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This thesis is divided into three chapters. The first chapter is a review of the literature methods utilised to date in the synthesis of non-racemic chiral sulfoxides, including resolution, stereospecific nucleophilic substitution at sulfur, asymmetric oxidation and enzymatic methods Also, this first chapter introduces briefly the palladium-catalysed allylic nucleophilic substitution reaction. It covers the nature of different factors which can influence on the enantiomeric excess. The second section deals with our approaches to the synthesis of potentially chelating sulfoxides of high enantio

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22

Learmonth, Robin Alec. "Studies in asymmetric synthesis." Thesis, Rhodes University, 1991. http://hdl.handle.net/10962/d1005018.

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The concept of combining two well established areas of organic chemistry, viz., organosilicon chemistry and the use of chiral auxiliaries, into a viable, alternative method of asymmetric synthesis has only very recently begun to receive attention. At the outset of this investigation, no asymmetric reactions of silyl enol ethers, chiral by virtue of optically active substituents on the silicon, had been reported. A range of novel chiral silyl enol ethers have thus been prepared from a variety of ketones, including pinacolone, cyclohexanone, and α-tetralone, and employing menthol, borneol, and c

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23

Donovan, Anthony Richard. "Aids in asymmetric synthesis." Thesis, Donovan, Anthony Richard (1998) Aids in asymmetric synthesis. PhD thesis, Murdoch University, 1998. https://researchrepository.murdoch.edu.au/id/eprint/51636/.

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The aims of this investigation were twofold. 1) Development of a practical diagnostic NMR reagent. 2) Novel C2 symmetric ligands for asymmetric synthesis. 1) Naturally occurring (+)-camphor was chosen as the basis for this programme ie the synthesis of homochiral isocyanates for use as NMR diagnostic reagents. Isocyanates 11, 39, 46 and 56 were synthesised via a wide range of synthetic techniques and these novel compounds and their precursors treated to comprehensive In addition all were subjected to reaction with suitable However, although these structural characterisation. alcohols to

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24

Razzino, Pasquale. "Asymmetric [alpha]-amino acid synthesis /." Title page, contents and abstract only, 1991. http://web4.library.adelaide.edu.au/theses/09PH/09phr279.pdf.

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25

Bentley, Scott Alexander. "Asymmetric conjugate addition reactions." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:9e619a66-6277-48c2-8a2e-24f8206e52b3.

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This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles. Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors. Chapter 2 explores the use of the N-benzyl-N-(α-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-(α- methylbenzyl)hydrazine and N -benzy

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26

Harrison, Michael John. "Asymmetric synthesis using chiral amines." Thesis, University of York, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.280371.

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27

Rustenhoven, Job Jesse. "Asymmetric synthesis of novel anthracyclinones." Thesis, University of Auckland, 1995. http://hdl.handle.net/2292/1903.

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The synthesis of novel C9-halogenated anthracyclinones by Lewis acid promoted cyclisations of ortho-methallyl anthraquinonyl chiral dioxanes has been investigated. Tin tetrachloride-N,N-dimethylformamide promoted cyclisation of the dioxane (30) proceeded with excellent stereoselectivity to give an 82% yield of the diastereomerically pure chlorotetracycle (78). Stronger Lewis acids gave poorer selectivity and boron trifluoride etherate reacted slowly with (30) but with high selectivity to give the diastereomerically pure fluorotetracycle (91) in 58% yield. The presence of a β-methoxy group in t

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28

Stratford, Peter William. "Asymmetric synthesis in heterogeneous systems." Thesis, Lancaster University, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.305943.

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29

Black, Antonia. "Catalytic asymmetric synthesis via organoboranes." Thesis, University of Oxford, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.410615.

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30

Smethurst, Chris. "Asymmetric synthesis of cyclic amines." Thesis, University of Oxford, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.298718.

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31

McKenna, Jeffrey M. "Asymmetric synthesis of #beta#-lactams." Thesis, University of Oxford, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.240681.

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32

Nicholson, Rebecca. "The asymmetric synthesis of hexoses." Thesis, University of Oxford, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.270229.

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33

Roger-Evans, Tania. "Asymmetric #alpha#-amino acid synthesis." Thesis, University of Oxford, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.279903.

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34

Kelly, Richard J. "Asymmetric synthesis of sperabillin D." Thesis, University of Oxford, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.300798.

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35

Yin, Jingda. "Enantiorecognition phenomena in asymmetric synthesis." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:89838860-52f1-4cdb-94e9-112d5bf0ef4b.

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This thesis is concerned with investigations into applications of double asymmetric induction and parallel kinetic resolution in asymmetric synthesis. Chapter 1 introduces enantiorecognition phenomena as a significant field in asymmetric synthesis. The main approaches in this field are described: double asymmetric induction, kinetic resolution, parallel kinetic resolution and dynamic kinetic resolution. Chapter 2 describes investigations into the use of double asymmetric induction as a mechanistic probe to elucidate the reactive conformation of enantiopure α,β-unsaturated esters (derived from

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36

Najah, Zaid. "Asymmetric synthesis using anthracene auxiliaries." Thesis, University of Sheffield, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.555128.

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Diels-Alder reaction conditions of the chiral anthracene auxiliary, 9-(l-methoxyethyl) anthracene and 2-cyclopenten-I-one were optimised using the microwave irradiation to give three regioisomers in 80: 12:8 ratio. Flash chromatography purification afforded the desired adduct in 45% yield. Subsequent asymmetric transformations on the major cycloadduct were performed in good yield with excellent levels of diastereoselectivity. Alkylation-reduction reactions sequence on the ketone cycloadduct furnished the desired ketones in 65-75% yield and up to 92:8 diastereoselectivity. Corresponding alcohol

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37

Treacy, Alan Bernard. "Nitrogen heterocycles in asymmetric synthesis." Thesis, Queen's University Belfast, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.361310.

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38

Cobb, Alexander John Andre. "Chiral diamines in asymmetric synthesis." Thesis, University College London (University of London), 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.395035.

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39

Devlin, Edward Charles. "New ligands for asymmetric synthesis." Thesis, University of Liverpool, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.428366.

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40

Morfitt, Charles Neil. "Diazo compounds in asymmetric synthesis." Thesis, University of Exeter, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.286531.

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41

Buck, Richard Tony. "Rhodium carbenoids in asymmetric synthesis." Thesis, University of Exeter, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.267219.

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42

Parr, Nigel. "Asymmetric #alpha#-amino acid synthesis." Thesis, University of Sussex, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.302251.

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43

Thomas, Stephen Patrick. "Phosphorus mediated asymmetric cyclopropane synthesis." Thesis, University of Cambridge, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.613118.

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44

Foster, Emma Marie. "Asymmetric synthesis of amino polyols." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:3393ed50-d465-491b-9270-c5f5228572ec.

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This thesis is concerned with the development of methodology for the asymmetric synthesis of a range of amino polyol containing compounds. Chapter 1 highlights the abundance of the amino polyol motif in nature, the wide range of biological activities displayed by amino polyol containing compounds, and their occurrence in drug molecules. A variety of different methods for the synthesis of stereodefined amino polyols is then discussed. Chapter 2 details a full investigation into the doubly diastereoselective conjugate addition reactions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)

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45

Ho, Wen-Bin. "The asymmetric synthesis of (-)-quinocarcin." Case Western Reserve University School of Graduate Studies / OhioLINK, 1992. http://rave.ohiolink.edu/etdc/view?acc_num=case1056475181.

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46

Brown, Richard Alan. "Asymmetric synthesis in neoteric solvents /." For electronic version search Digital dissertations database. Restricted to UC campuses. Access is free to UC campus dissertations, 2003. http://uclibs.org/PID/11984.

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47

Suzuka, Toshimasa. "Asymmetric Synthesis of Cyclopentadiene Derivatives." 京都大学 (Kyoto University), 2003. http://hdl.handle.net/2433/149096.

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48

Lu, Chin-Wei. "Synthesis of Asymmetric Phthalocyanine Derivatives." Diss., The University of Arizona, 2013. http://hdl.handle.net/10150/312651.

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The work in this dissertation describes improved methods of asymmetrically substituted Pc derivative synthesis addressing some currently encountered problems including: (1) the need for facile synthesis of asymmetric Pc/Nc hybrids; (2) a lack of general methods for producing asymmetric Pc materials with structural diversity. Chapter 1 provides a concise review on Pc and Pc/perylenediimide (PDI) derivatives that have been reported as a part of architecture in monochromophoric or multichromophoric molecules for energy and charge transfer studies. In addition, the intrinsic electronic and photop

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49

Tye, Heather. "Novel diazaphospholidines for asymmetric synthesis." Thesis, University of Bath, 1996. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.320431.

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50

Foust, Benjamin John. "Synthesis of asymmetric phosphonate prodrugs." Diss., University of Iowa, 2019. https://ir.uiowa.edu/etd/6734.

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The isoprenoid biosynthetic pathway is an essential metabolic system that is responsible for the production of one of the largest and most diverse ranges of biomolecules ever identified. The termini of this pathway include: fat-soluble vitamins, cholesterol, reproductive hormones, and components of cellular signal transduction and electron transport pathways. With such a diverse set of biologically important metabolites, it has become one of the most targeted pathways for study in human pathology. Earlier pharmaceutical development has yielded clinically relevant classes of compounds that impa

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