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Dissertations / Theses on the topic 'Chiral amino alcohols'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

Henriquez, Morales Maria-Jose. "Synthetic biology routes to production of chiral amino-alcohols in Pichia pastoris." Thesis, University College London (University of London), 2018. http://discovery.ucl.ac.uk/10050823/.

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Pichia pastoris (P. pastoris) is an attractive industrial host cell due to its ability to grow up to 60% wet cell weight (WCW) by volume, a far higher level of biomass than the typical values reached by Escherichia coli (E. coli) and Saccharomyces cerevisiae (S. cerevisiae). This thesis seeks to explore how the genetic tractability and high cell densities characteristic of P. pastoris can be exploited to intensify whole-cell biocatalysis. Chiral amino alcohols such as 2-amino-1,3,4-butanetriol (ABT) are key building blocks of small molecule pharmaceuticals and have previously been produced by

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2

Adjei, Bernard Louis. "The Synthesis and Characterization of Diastereomeric Phosphorus Mustards Derived from Chiral Amino Alcohol." Youngstown State University / OhioLINK, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1566419465752266.

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3

Cakir, Esen. "Synthesis Of Novel Chiral N,n-dialkyl Substituted 1,4-amino Alcohols And Applications In Asymmetric Transformation Reactions." Master's thesis, METU, 2007. http://etd.lib.metu.edu.tr/upload/12608484/index.pdf.

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Amino alcohols are valuable bioactive substances and frequently used as chiral catalyst in various asymmetric transformation reactions. In the synthetic route, the asymmetric synthesis of novel chiral N,N-dialkyl substituted chiral 1,4-amino alcohols are performed starting with meso-anhydride 38. Quinine-mediated desymmetrization of the anhydride with methanol afforded (2S,3R)-cis-monoester 39 with a high enantiomeric excess (up to 98% ee). Chemoselective amidation of hemiester with various N,N-dialkyl substituted amines resulted in amido esters and they were subjected to LAH reduction to affo

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4

Gunler, Zeynep Inci. "Synthesis Of N-(2-propylphenyl) Substituted Chiral Amino Alcohols And Their Usage In Enantioselective Diethylzinc Addition Reactions." Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613001/index.pdf.

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Chiral 1,2-amino alcohols were synthesized via newly developed &ldquo<br>intramolecular unsaturation transfer&rdquo<br>using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were screened for the synthesized chiral ligands. In diethylzinc addition to be

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5

Powell, Magdalena Elizabeth. "Investigating three component protocols to determine the enantiopurity of chiral amines and amino alcohols using 1H and 19F NMR spectroscopy." Thesis, University of Bath, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.579515.

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This report describes the development of simple three-component chiral derivatisation protocols to determine the enantiopurity of a range of chiral amines and amino alcohols using IH and 19p NMR spectroscopic techniques. In each of the protocols described a 2-formylphenylboronic acid core participates in tandem imine formation with an amine moiety and boronate ester condensation with a chiral diol to afford a pair of diastereomeric imino-boronate esters. These derivatives show distinguishable resonances in NMR spectra; the relative integrals of which reflect the enantiopurity of the starting a

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6

Sehl, Torsten [Verfasser], Martina [Akademischer Betreuer] Pohl, and Jörg [Akademischer Betreuer] Pietruszka. "2-Steps in 1-pot: enzyme cascades for the synthesis of chiral vicinal amino alcohols / Torsten Sehl. Gutachter: Martina Pohl ; Jörg Pietruszka." Düsseldorf : Universitäts- und Landesbibliothek der Heinrich-Heine-Universität Düsseldorf, 2014. http://d-nb.info/1051734681/34.

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7

Buchanan, D. J. "Diastereoselective oxy-Michael addition of a new chiral water equivalent to electron deficient alkenes : synthesis of 1,2-amino alcohols and b-hydroxy malonates." Thesis, University of Cambridge, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.597051.

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Chapters 1 and 2: An introduction to the intermolecular oxy-Michael reaction and a brief overview of the methods used to synthesise 1,2-amino alcohols. Chapter 3: An oxy-Michael reaction was developed whereby the addition of (<i>S</i>)-6-methyltetrahydropyran into a,b-unsaturated monosubstituted nitro compounds allowed rapid access to synthetically important 1,2-amino alcohols. Chapter 4: A logical advancement of the oxy-Michael addition was the addition into a,b-unsaturated disubstituted nitro compounds. These molecules were also converted into the corresponding 1,2-amino alcohols. In additio

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8

Pinho, Pedro. "Development and application of new chiral -amino alcohols in synthesis and catalysis : Use of 2-azanorboryl-3-methanols as common intermediates in synthesis and catalysis." Doctoral thesis, Uppsala universitet, Kemiska institutionen, 2001. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-1267.

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The development and application of unnatural amino alcohols,prepared via hetero-Diels-Alder reactions,in synthesis and catalysis is described.The studies are concerned with the [i]scope of the hetero-Diels-Alder reaction and preparation of important intermediates in the synthesis of antiviral agents,[ii ]application of amino alcohols in the ruthenium transfer hydrogenation of ketones,[iii ]use of similar precursors in the in situ generation of oxazaborolidines for reduction of ketones,and [iv] development and application of new chiral auxiliaries for dialkylzinc additions to activated imines,

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9

Canbolat, Eylem. "Organocatalytic Resolution Of Racemic Alpha Azido Ketones." Master's thesis, METU, 2012. http://etd.lib.metu.edu.tr/upload/12614602/index.pdf.

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Chiral cyclic alpha azido ketones are very important compounds in organic chemistry. Because, the reduced forms of them are amino alcohols and these amino alcohols are interesting compounds for their biological activities. They have some pharmaceutical activities such as: potassium channel open up properties, treatment of central nervous system, antihypertensive properties, the agent of dopamin receptor activator, hypolipemic agent and dopamine agonist. These types of compounds have highly acidic alpha-protons, and many kinds of reactions can be performed with them. In this study, mainly, sel

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10

Villegas, Torres M. F. "Design and characterization of novel biocatalytic cascades for chiral amino alcohol synthesis." Thesis, University College London (University of London), 2014. http://discovery.ucl.ac.uk/1425692/.

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Chiral amino alcohols are building blocks of several pharmaceuticals such as antibiotics, and retrovirals. De novo biocatalytic strategies have been developed for their production as chemical synthesis presents several challenges in establishing chiral centres. One of the successful approaches previously implemented in the Biochemical Engineering Department is the coupling of a transketolase with a transaminase step. This scheme depends on the use of hydroxypyruvate (HPA) and methylbenzylamine (MBA), which are expensive non-natural substrates limiting both the application of the pathway on an

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11

Sunbul, Murat. "Asymmetric Synthesis Of Norbornene Based 1,4-amino Alcohol Derivatives And Applications In Asymmetric Transformations." Master's thesis, METU, 2005. http://etd.lib.metu.edu.tr/upload/12606174/index.pdf.

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The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. The chiral ligands (2S,3R)-(-)-35, (2S,3R)-(+)-36 and (2S,3R)-(-)-37 were subjected to

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12

Odabas, Serhat. "Asymmetric Synthesis Of N-aryl Substituted Chiral 1,4-amino Alcohol Derivatives And Applications In Various Asymmetric Transformation Reactions." Master's thesis, METU, 2007. http://etd.lib.metu.edu.tr/upload/12608489/index.pdf.

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The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemicalb yield. The quinine-mediated desymmetrization of meso-anhydride 51 with methanol gave (2S,3R)-(-)-cis-monoester 52. The hemiester

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13

Erdem, Mine. "Asymmetric Synthesis Of Norbornene Based 1,4-aminoalcohol Derivatives And Applications In Asymmetric Diethylzinc Reactions." Master's thesis, METU, 2007. http://etd.lib.metu.edu.tr/upload/12608318/index.pdf.

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The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this resulting compound with HMPTA was performed and by keeping the amine group constant, the amido

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14

黎方國. "Chiral recognition mechanisms of amino acids and amino alcohols on chiral stationary phases containing two chiral centers consisting of phenylalanine and naphthylethylamine." Thesis, 1995. http://ndltd.ncl.edu.tw/handle/13703092490082418235.

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15

Huang, Wei Ming, та 黃偉銘. "Asymmetric Addition Reactions Catalyzed by Camphor-Derived Chiral β-Amino Alcohols and β-Amino Thiols". Thesis, 2015. http://ndltd.ncl.edu.tw/handle/75m7z7.

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博士<br>國立清華大學<br>化學系<br>104<br>因申請專利緣故，資料延後公開 This thesis reports the application of camphor-derived chiral β-amino alcohols and β-amino thiols in asymmetric addition reactions. In the first part, a series of chiral amino alcohols 12a–l has been synthesized and used in the enantioselective addition of dialkylzinc to aromatic aldimines. Application of the optimal chiral ligand 12a (10 mol%) with methanol (1.8 equiv.) as the additive to activate the reaction of aromatic aldimines with diethylzinc and dimethylzinc resulted in high yields (60–92%) and enantioselectivities (84–96% ee). In th

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16

Shang-Jer, Wu, and 吳尚哲. "Applications of chiral amino-alcohols in asymmetric additions of diethylzinc to aldehydes." Thesis, 2000. http://ndltd.ncl.edu.tw/handle/86010056235545483347.

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17

day, danny, та 戴森地. "A study of Asymmetric Reformatsky Reaction of α-iodoester using chiral amino alcohols derivated form amino acids". Thesis, 2005. http://ndltd.ncl.edu.tw/handle/88507915134795521234.

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碩士<br>國立中興大學<br>化學系<br>93<br>The use of a series of chiral amino-alcohols as ligand to control the stereoselectivity of Reformatsky reaction has been examined. We found that, the β-hydroxy esters were prepared from asymmetric Reformatsky reactions with good enatioselectivity up to 90% e.e..

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18

詹淑怡. "Asymmetric Reformatsky Reaction Catalyzed by Camphor-derives β-Amino Alcohols as Chiral Ligands". Thesis, 2012. http://ndltd.ncl.edu.tw/handle/72168733135956251457.

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19

Chu, Wei-Lun, and 祝偉倫. "Synthesis of Inherently Chiral Azobiscalix[4]crowns and Their Enantiomeric Recognition of Amino Alcohols." Thesis, 2015. http://ndltd.ncl.edu.tw/handle/zddr85.

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碩士<br>國立交通大學<br>應用化學系碩博士班<br>103<br>The research goal of this thesis is the synthesis of inherently chiral azobiscalix[8]crown and its chiral recogonition toward aminoalcohols. First, in the condition of NaH as a base and DMF as a solvent, we could obtain 1,3-to-1,2 double bridged biscalix[4]arene compound 7b in high selectivity, which is a good precursor for inherently chiral calix[4]raene. After acidification and adding diazo functional group on 7b, we could obtain inherently chiral compound 12b in 8% yield. UV-vis screening experiment was carried out by adding aminoalcohol compounds to race

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20

Wu, Wei-Hsin, and 吳偉新. "Synthesis of Binaphthyl-Derived Calix[4]crowns and Their Chiral Recognition of Amino Alcohols." Thesis, 2010. http://ndltd.ncl.edu.tw/handle/05626114691922368911.

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碩士<br>國立交通大學<br>應用化學研究所<br>98<br>In this thesis, a series of binaphthyl-derived chiral calix[4]crowns were synthesized and their recognition abilities toward chiral amino alcohols and metal ions were studied. We have synthesized a series of (S)-(-)-binaphthyl-appended calix[4]crown-n ether (n = 6, 8) 41-49, which were substituted with mono- or proximal bis-carboxyl groups. The complexation properties of binaphthyl hosts (S)-(-)-44a-b and (S)-(-)-49a toward chiral amines, amino alcohols, alcohols and diols 50-57 were investigated by the UV-visible, fluorescence and CD spectroscopies. Possible

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21

Su, Kurn-Yu, and 蘇冠宇. "Ⅰ. Study of one-pot synthesis of some acyl alcohols starting from ketonesⅡ. Chiral methyl[3.2.1]bicyclic amino alcohol as organocatalyate for asymmetric addition reaction." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/60035438721566294638.

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碩士<br>國立暨南國際大學<br>應用化學系<br>101<br>Ⅰ、In our laboratory, we had synthesized of 1-acyl-1-indanols via three steps1, before. First, a wittig reaction of indanone molecules with benzyltriphenyl-phosphoniumchloride, in the presence of butyl lithium, furnished phenylmethyl alkene. Then, dihydroxylation of phenylmethyl alkene with Osmium tetraoxide and T.M.O. reaction gave a diol compound, in which the secondary group was further oxidized to carbonyl. Poor overall yield via three steps. Therefore, we use 1,3-dithiane as areagent for one-pot synthesis. Thus, in a one-pot synthesis reaction. First, at l

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22

Peng, Bo-Chun, and 彭柏淳. "I. Syntheses, Self-assembly and Thermodynamics of Cis-Trans Isomerization of Azobenzene Bridged Biscalix[4]arenes with 1,2-Alternate and Partial Cone Conformations. II. Synthesis of Chiral Azocalix[4]arene and Its Chiral Recognition of Amino Alcohols." Thesis, 2019. http://ndltd.ncl.edu.tw/handle/t9m83j.

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碩士<br>國立交通大學<br>應用化學系碩博士班<br>108<br>In the first part, we have synthesized calix[4]arene conformational isomers using metal template effect and azobenzene to bridge the calix[4]arenes by 1,3-dipolar cycloaddition and click chemistry. The gelation properties were tested to are whether different conformational isomers will have better packing ability or not. According to the results, compound (+/-)26, 27 and 30 could not form gel in any solvent. We also studied the thermally induced cis-trans isomerization of compounds (+/-)26, 27 and 30, and found that their activation energies were around 21.0

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23

Mishra, Sandeep Kumar. "Study of Diverse Chemical Problems by NMR and the Design of Novel Two Dimensional Techniques." Thesis, 2017. http://etd.iisc.ernet.in/2005/3558.

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The research work reported in this thesis is focused on the chiral analysis, quantification of enantiomeric composition, assignment of absolute configuration of molecules with chosen functional groups. The weak intra-molecular hydrogen bonding interactions are detected by exploiting several multinuclear and multi-dimensional techniques. Pulse sequences have been designed to manipulate the spin dynamics to derive specific information from the complex NMR spectra encountered in diverse situations. Broadly, the thesis can be classified in to three sections. The section I containing two chapters r

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24

Shen, Ying-Ying, та 沈盈瑩. "The Synthesis and Application of Camphor Derived Chiral γ-Amido Thiol and β-Amino Alcohol Ligand". Thesis, 2013. http://ndltd.ncl.edu.tw/handle/3f9sj4.

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碩士<br>國立清華大學<br>化學系<br>101<br>This thesis dealt with the development of new chiral ligands, γ-amido thiol (10) and β-amino alcohol (11), based on γ-amino thiol(-)-MITH (2) and β- amino alcohol (+)-MINBOL (3), respectively. Furthermore, this thesis also dealt with the application of β-amino alcohol (11) in catalytic asymmetric addition reactions of diethylzinc and arylzinc to aldehydes to construct chiral secondary alcohols. Asymmetric ethylation using a stock solution of diethylzinc (1.1 M in toluene) was carried out in the presence of 0.5 mol % of β-amino alcohol (11) at room temperature and

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25

Guu, Jan-An, and 古振安. "Studies on the Enantioselective Reaction of Chiral Lithium ynthesis of Chiral Amino Alcohol." Thesis, 1993. http://ndltd.ncl.edu.tw/handle/25856508031154057706.

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26

Mishra, Sandeep Kumar. "Study of Diverse Chemical Problems by NMR and the Design of Novel Two Dimensional Techniques." Thesis, 2017. http://etd.iisc.ac.in/handle/2005/3619.

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The research work reported in this thesis is focused on the chiral analysis, quantification of enantiomeric composition, assignment of absolute configuration of molecules with chosen functional groups. The weak intra-molecular hydrogen bonding interactions are detected by exploiting several multinuclear and multi-dimensional techniques. Pulse sequences have been designed to manipulate the spin dynamics to derive specific information from the complex NMR spectra encountered in diverse situations. Broadly, the thesis can be classified in to three sections. The section I containing two chapters r

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27

Yang, Soon Ching, and 楊順清. "Asymmetric conjugate addition of diethylzinc to chalcone with chiral amino alcohol and amino thiol derivatives." Thesis, 2003. http://ndltd.ncl.edu.tw/handle/41015467962610937302.

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碩士<br>國立中興大學<br>化學系<br>91<br>Abstrate The research in this thesis focuses on how using amino acid as a starting material, we produce chiral amino alcohol and chiral amino thiol to be a chiral catalyst. With the co-existence of Ni complexes, causing the catalysis of diethylzinc, we proceed 1,4-addition reaction on chalcone. The result show that under the condition of —30°C reaction temperature, we can get the enantioselectivity up to 92.5% e.e. In the study of chiral ligand, we have seen all kinds of amino alcohol in many references, but all of them used N atom and O ato

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28

Jheng, Jing-Yan, та 鄭敬嚴. "Catalytic Asymmetric Reduction of Acetophenone by Ru and Chiral Camphor-derivatived β-amino alcohol". Thesis, 2006. http://ndltd.ncl.edu.tw/handle/66714182051593135071.

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碩士<br>國立成功大學<br>化學系碩博士班<br>94<br>Camphor is widely applied to catalytic asymmetric synthesis because of it’s two nature chiral center. We design and synthesis β-amino alcohol from camphor by a very highly stereoselecviv -e route and then we modify several different substituent group on the nitrogen. We achieve the goal by reductive amination because we want to get secondary amines. Instead of imines, we get the 5 member oxazolidine rings. Then open the rings, we obtain the desired Compound. Finally we apply the β-amino alcohols to the rutheniu catalytic asymmetric synthesis.

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29

Tseng, Chih-Hao, та 曾志豪. "The Study on Asymmetric Nucleophilic Addition Reaction Catalyzed by Camphor Derived Chiral β-Amino Alcohol and β-Amino Thiol". Thesis, 2011. http://ndltd.ncl.edu.tw/handle/45559250610104053101.

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博士<br>國立清華大學<br>化學系<br>99<br>This thesis, divided into three parts, is concerned with the application of camphor-derived chiral β-amino alcohol or β-amino thiol in catalytic asymmetric conjugate addition of carbon nucleophiles to α,β-unsaturated systems and asymmetric addition reactions of organozinc to carbonyl compounds. The first part has discuss the complex of (+)-MINBOL 28 and Ni(acac)2 (12.5 mol% and 0.5 mol% respectively) catalyzes enantioselective conjugate 1,4-addition of dialkylzinc to α,β-unsaturated enones in propionitrile, giving the corresponding chiral Michael adducts in high e

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30

Lien, Chia-ling, and 連家聆. "Synthetic Studies for the Preparation of Chiral Amino Alcohol and Cyclic Phosphonates Starting from (-)-Pinene." Thesis, 2006. http://ndltd.ncl.edu.tw/handle/50567576862798354480.

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碩士<br>朝陽科技大學<br>應用化學系碩士班<br>95<br>For the last two decades it has shown that α-pinene is a good source for the synthesis of various chiral materials which resulted in the commerciallizations of, for example, (+)- and (-)-2-Hydroxypinan-3-one. Recently, enantiomerically pure amino alchohols, such as (+)- and (-)-3-Amino-2- Hydroxypinane, have also been reported. However, little has been mentioned for the synthesis of enantiomerically pure N-substituted aminoalcohols, except the works done by Karolak-Wojciechowska in 1989, in which whether the N-substituted amino alcohols have been prepared with

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31

徐秀霞. "Regioselective and Stereoselective Nitrile Oxide Cycloaddition to Chiral Unsaturated Acetals Prepared from a Camphor-based Amino Alcohol." Thesis, 1994. http://ndltd.ncl.edu.tw/handle/96085218005570987110.

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32

Chen, An Jyun, та 陳安君. "The Study on Asymmetric Tandem Michael/Mannich Reaction of Diethylzinc to trans-chalcone by Camphor Derived Chiral β-Amino Alcohol". Thesis, 2015. http://ndltd.ncl.edu.tw/handle/9qj747.

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碩士<br>國立清華大學<br>化學系<br>103<br>The thesis dealt with the application of camphor-derived chiral ß-amino alcohol in catalytic asymmetric tandem Michael/Mannich reaction of diethylzinc to trans-chalcone. Utilizing the complex of (+)-MINBOL 6 (12.5 mol%) and Ni(acac)2 (0.5 mol%) catalyzed the enantioselective conjugate 1,4-addition of diethylzinc to trans-chalcone 12 afforded chiral zinc enolate 13. The chiral zinc enolate 13 was further reacted with imine 14a-k, which furnished Major products ß-amino ketone 4a-k (1S,2R,3S) with high enantioselectivity and good yield.

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33

Mishra, Sandeep Kumar. "Study of Diverse Chemical Problems by NMR and the Design of Novel Two Dimensional Techniques." Thesis, 2017. http://etd.iisc.ac.in/handle/2005/3558.

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The research work reported in this thesis is focused on the chiral analysis, quantification of enantiomeric composition, assignment of absolute configuration of molecules with chosen functional groups. The weak intra-molecular hydrogen bonding interactions are detected by exploiting several multinuclear and multi-dimensional techniques. Pulse sequences have been designed to manipulate the spin dynamics to derive specific information from the complex NMR spectra encountered in diverse situations. Broadly, the thesis can be classified in to three sections. The section I containing two chapters r

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