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Journal articles on the topic 'Chiral Carboxylic Acid'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 September 2023

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1

Min, Chang, and Daniel Seidel. "Asymmetric Brønsted acid catalysis with chiral carboxylic acids." Chemical Society Reviews 46, no. 19 (2017): 5889–902. http://dx.doi.org/10.1039/c6cs00239k.

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2

Lemmerer, Andreas, Nikoletta B. Báthori, and Susan A. Bourne. "Chiral carboxylic acids and their effects on melting-point behaviour in co-crystals with isonicotinamide." Acta Crystallographica Section B Structural Science 64, no. 6 (2008): 780–90. http://dx.doi.org/10.1107/s0108768108034526.

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The crystal structures of co-crystals of two systems of chiral carboxylic acids, optically active and racemic 2-phenylpropionic acid and 2-phenylbutyric acid, with isonicotinamide are reported to investigate the effects of the chirality of the chiral carboxylic acids on the melting point of the co-crystal complexes. It was found that the racemic co-crystal has a higher melting point than the optically active co-crystal, which correlates with the denser packing arrangement inherent in centrosymmetric space groups.
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3

Moloney, Mark G., Diana R. Paul, Russell M. Thompson, and Emma Wright. "Chiral carboxylic acid ligands derived from camphoric acid." Tetrahedron: Asymmetry 7, no. 9 (1996): 2551–62. http://dx.doi.org/10.1016/0957-4166(96)00328-x.

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4

Nagatomo, Nao, Hisashi Oishi, Yutaka Kuwahara, et al. "Enantioselective Self-Assembled Nanofibrillar Network with Glutamide-Based Organogelator." Nanomaterials 11, no. 6 (2021): 1376. http://dx.doi.org/10.3390/nano11061376.

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A chiral molecular gelation system, as a chiral host, was used to effectively realize enantioselectivity using the simple carboxylic acid functional group. For this purpose, an L-glutamic-acid-based lipidic amphiphile (G-CA) with a carboxylic head group was selected and its responsiveness to cationic guest molecules was investigated. The dispersion morphology of G-CA in its solution state was examined by confocal and transmission electron microscopies, while interactions between the G-CA, as the host system, and guest molecules were evaluated by UV-visible, circular dichroism, and fluorescence
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5

Kühl, Olaf, Stephan Millinghaus, and Philipp Wehage. "Functionalised, chiral imidazolium compounds from proteinogenic amino acids." Open Chemistry 8, no. 6 (2010): 1223–26. http://dx.doi.org/10.2478/s11532-010-0097-9.

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6

Li, Bao Hui. "Chiral Separation of Non-Natural Amide Amino Acid by Capillary Electrophoresis with CD Derivations as Chiral Selective Material." Advanced Materials Research 554-556 (July 2012): 824–27. http://dx.doi.org/10.4028/www.scientific.net/amr.554-556.824.

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A capillary electrophoresis (CE) method for the separation of four kinds of enantiomers of non-natural carboxylic amino acid was built while hydroxypropyl-β- cyclodextrin (HP-β-CD) derivations as chiral selective material. Several different β-CD derivatives were tested for the chiral separation of non-natural carboxylic amino acid, and it was proved that HP-β-CD could show better chiral selectivity. The separation of enantiomers of amino acid was obtained by CE in a 50-μm i.d.×60 cm (effective length 45 cm) fused-silica capillary at 18 kV voltage, while 10 mM phosphate acted as running buffer
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7

Li, Bao Hui, and Bao Juan Tian. "Chiral Separation of Non-Natural Carboxylic Amino Acid by Capillary Electrophoresis with CD Derivations as Chiral Selective Material." Applied Mechanics and Materials 130-134 (October 2011): 4126–29. http://dx.doi.org/10.4028/www.scientific.net/amm.130-134.4126.

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A capillary electrophoresis (CE) method for the separation of four kinds of enantiomers of non-natural carboxylic amino acid was built while hydroxypropyl-β-cyclodextrin (HP-β-CD) derivations as chiral selective material. Several different β-CD derivatives were tested for the chiral separation of non-natural carboxylic amino acid, and it was proved that HP-β-CD could show better chiral selectivity. The separation of enantiomers of amino acid was obtained by CE in a 50-μm i.d.×60 cm (effective length 45 cm) fused-silica capillary at 18 kV voltage, while 10 mM phosphate acted as running buffer a
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8

Maeda, Hajime, Masayuki Iida, Daisuke Ogawa, and Kazuhiko Mizuno. "Enantioselective Protonation of Radical Anion Intermediates in Photoallylation and Photoreduction Reactions of 3,3-Diaryl-1,1-dicyano-2-methylprop-1-ene with Allyltrimethylsilane." Molecules 24, no. 14 (2019): 2677. http://dx.doi.org/10.3390/molecules24142677.

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Photoreactions of acetonitrile solutions of 3,3-diaryl-1,1-dicyano-2-methylprop-1-enes (1a–c) with allyltrimethylsilane (2) in the presence of phenanthrene as a photoredox catalyst and acetic acid as a proton source formed photoallylation (3) and photoreduction (4) products via photoinduced electron transfer pathways. When (S)-mandelic acid was used as the proton source, the reactions proceeded with 3.4 and 4.8 %ee for formation of 3 and 4, respectively. The results of studies of the effect of aryl ring substituents and several chiral carboxylic acids suggested that the enantioselectivities of
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9

Duke, CC, and RJ Wells. "Investigation of Readily Available Chiral Compounds for Preparative Scale Resolutions." Australian Journal of Chemistry 40, no. 10 (1987): 1641. http://dx.doi.org/10.1071/ch9871641.

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Diastereoisomeric esters were formed by reaction of racemic carboxylic acids with the readily available hydroxy lactone derivatives, 2,3-O-isopropylidene-D(+)-ribono-l,4-lactone, D(-)-2- hydroxy-3,3-dimethylbutyro-1,4-lactone (D(-)-pantolactone) and 1,2-O-isopropylidene-(+)-α-D-glucofuranurono-6,3-lactone. In all cases separation of the diastereoisomeric esters was achieved by crystallization and/or chromatography. Purity of the diastereoisomers could be determined by h.p.l.c. or by 1H n.m.r. Hydrolysis under mild basic conditions followed by treatment with acid gave optically pure carboxylic
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10

Balaji, Pandur Venkatesan, and Srinivasan Chandrasekaran. "Geminal Difunctionalization of Vinylarenes: Concise Synthesis of 1,3-Dioxolan-4-ones." Synlett 30, no. 20 (2019): 2263–67. http://dx.doi.org/10.1055/s-0039-1690250.

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We report a straightforward method for the synthesis of five-membered 1,3-dioxolan-4-ones by an unprecedented oxidative alkene geminal difunctionalization strategy using α-hydroxy carboxylic acids. Under the geminal oxidative addition conditions, various substituted α-hydroxy carboxylic acids and styrenes containing a variety of substituents, including β-substituted styrenes, were effectively coupled regioselectively (anti-Markovnikov) with an isobutyl-substituted chiral α-hydroxy carboxylic acid, providing an annulation with excellent dia­­stereoselectivity. An aryl migration in the semipinac
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11

Vargová, Denisa, Juana M. Pérez, Syuzanna R. Harutyunyan, and Radovan Šebesta. "Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles." Chemical Communications 55, no. 78 (2019): 11766–69. http://dx.doi.org/10.1039/c9cc05041h.

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Chiral enolates generated by asymmetric Cu-catalyzed and Lewis acid promoted conjugate addition of Grignard reagents to unsaturated amides, alkenylheterocycles, and carboxylic acids are trapped with cations, activated alkenes, or bromine.
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12

Katoh, Tadashi, Koichi Narita, Noel Sayar, Ken Saijo, and Chikashi Ishioka. "A Concise Approach for Producing Optically Pure Carboxylic Acid Segments for the Synthesis of Bicyclic Depsipeptide Histone Deacetylase Inhibitors." Synthesis 51, no. 06 (2019): 1408–18. http://dx.doi.org/10.1055/s-0037-1612059.

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Optically pure carboxylic acid segments, which are common key intermediates for the synthesis of naturally occurring bicyclic depsipeptide histone deacetylase inhibitors, have been produced efficiently. The method features the chromatographic separation of two diastereomers, which were formed by direct amide condensation of racemic (3RS,4E)-3-hydroxy-7-mercaptohept-4-enoic acid (rac-Hmh) with chiral amino acids. This approach offers a reliable and practical method for producing optically pure carboxylic acid segments, which can facilitate easier access to important anticancer agents derived fr
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13

Mou, Qi, Ruyuan Zhao, Ruihan Niu, et al. "Cp*Ir(iii)/chiral carboxylic acid-catalyzed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates." Organic Chemistry Frontiers 8, no. 24 (2021): 6923–30. http://dx.doi.org/10.1039/d1qo01344k.

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An achiral Cp*Ir(iii)/chiral carboxylic acid-catalysed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates was achieved, providing planar chiral alkylated ferrocenes in up to 94 : 6 er.
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14

Martens, Jürgen, Stefan Lübben та Walter Schwarting. "Stereoselective Reaction Mass Spectrometry with Cyclic α-Amino Acids". Zeitschrift für Naturforschung B 46, № 3 (1991): 320–25. http://dx.doi.org/10.1515/znb-1991-0312.

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Stereoselective reaction mass spectrometry in the chemical ionization (isobutane) mode has been used to detect the absolute configuration of enantiomerically pure cyclic α-amino acids. Thus, an enantiomerically pure cyclic α-amino acid was allowed to react on a micromole level with both enantiomers of a chiral selector and the mass spectra were detected. The relative abundances of characteristic ions formed by the diastereoselective reaction between the α-amino acid and the chiral selector of the same configuration were much higher than those ions formed by the α-amino acid and the chiral sele
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15

Pan, Chongqing, Si-Yong Yin, Qing Gu, and Shu-Li You. "CpxM(iii)-catalyzed enantioselective C–H functionalization through migratory insertion of metal–carbenes/nitrenes." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7264–75. http://dx.doi.org/10.1039/d1ob01248g.

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In this review, we highlight the developments in chiral CpxM(iii) complexes or achiral CpxM(iii) complexes/chiral carboxylic acid-catalyzed enantioselective C–H functionalization reactions through migratory insertion of metal–carbenes/nitrenes.
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16

Otsuka, Yuta, Yuto Shimazaki, Hitoshi Nagaoka, Keiji Maruoka та Takuya Hashimoto. "Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides". Synlett 30, № 14 (2019): 1679–82. http://dx.doi.org/10.1055/s-0039-1690109.

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Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization of N-methoxy β,γ-unsaturated amides
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17

Bünnemann, Karoline, та Christian Merten. "Solvation of a chiral carboxylic acid: effects of hydrogen bonding on the IR and VCD spectra of α-methoxyphenylacetic acid". Physical Chemistry Chemical Physics 19, № 29 (2017): 18948–56. http://dx.doi.org/10.1039/c7cp02049j.

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18

Uraguchi, Daisuke, Tomohito Kizu, Yuki Ohira та Takashi Ooi. "Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis". Chem. Commun. 50, № 88 (2014): 13489–91. http://dx.doi.org/10.1039/c4cc06081d.

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P-Spiro chiral diaminodioxaphosphonium ion discriminates the enantiofaces of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals by the recognition of the electronic difference between two substituents of the ketene disilyl acetal in the proton-transfer event.
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19

MOLONEY, M. G., D. R. PAUL, R. M. THOMPSON, and E. WRIGHT. "ChemInform Abstract: Chiral Carboxylic Acid Ligands Derived from Comphoric Acid." ChemInform 28, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199703059.

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20

Laaksonen, Tiina, Sami Heikkinen, and Kristiina Wähälä. "Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition." Organic & Biomolecular Chemistry 13, no. 42 (2015): 10548–55. http://dx.doi.org/10.1039/c5ob01667c.

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(+)-Dehydroabietylamine (1a), the novel derivatives (2a–6a) and their NTf<sub>2</sub> salts (1b–6b) were tested as chiral NMR solvating agents for the resolution of enantiomers of Mosher's acid and other carboxylic acids, and their n-Bu<sub>4</sub>N salts.
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21

Salerno, Francesco, José Augusto Berrocal, Andreas T. Haedler, Francesco Zinna, E. W. Meijer, and Lorenzo Di Bari. "Highly circularly polarized broad-band emission from chiral naphthalene diimide-based supramolecular aggregates." Journal of Materials Chemistry C 5, no. 14 (2017): 3609–15. http://dx.doi.org/10.1039/c7tc00281e.

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22

Odounga Odounga, Jean-Eudes, and Nikoletta B. Báthori. "Systematic comparison of racemic and enantiopure multicomponent crystals of phenylsuccinic acid—the role of chirality." CrystEngComm 22, no. 12 (2020): 2208–18. http://dx.doi.org/10.1039/d0ce00072h.

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Comparison of binary cocrystals of chiral and racemic carboxylic acids showed that the introduction of chiral building blocks may lead to the formation of subclasses of multicomponent crystals with unique Z′′/Z<sup>r</sup> values combined with complex protonation stages of the molecules.
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23

Sørensen, Henning Osholm, and Sine Larsen. "Hydrogen bonding in enantiomeric versus racemic mono-carboxylic acids; a case study of 2-phenoxypropionic acid." Acta Crystallographica Section B Structural Science 59, no. 1 (2003): 132–40. http://dx.doi.org/10.1107/s0108768102022085.

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The structural and thermodynamic backgrounds for the crystallization behaviour of racemates have been investigated using 2-phenoxypropionic acid (PPA) as an example. The racemate of PPA behaves normally and forms a racemic compound that has a higher melting point and is denser than the enantiomer. Low-temperature crystal structures of the pure enantiomer, the enantiomer cocrystallized with n-alkanes and the racemic acid showed that hydrogen-bonded dimers that form over crystallographic symmetry elements exist in all but the structure of the pure enantiomer. A database search for optically pure
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24

Pettigrew, Jeremy D., Rebecca P. Freeman, and Peter D. Wilson. "Total synthesis of (–)-xyloketal D and its enantiomer — Confirmation of absolute stereochemistry." Canadian Journal of Chemistry 82, no. 11 (2004): 1640–48. http://dx.doi.org/10.1139/v04-138.

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The total synthesis of (–)-xyloketal D and its enantiomer have been achieved by the reaction of an ortho-quinone methide with (4R)- and (4S)-4,5-dihydro-2,4-dimethylfuran via a diastereoselective inverse electron demand Diels–Alder reaction. This total synthesis confirmed the absolute stereochemistry of the natural product. The ortho-quinone methide was generated by reaction of an appropriately functionalized Mannich base with methyl iodide. The Mannich base was prepared in one step from 2,4-dihydroxyacetophenone, formaldehyde, and morpholine. The enantiomeric dihydrofurans were prepared from
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25

Savich, Carolyn Z., and Joseph M. Tanski. "Crystallographic and spectroscopic characterization of racemic Mosher's Acid." Acta Crystallographica Section E Crystallographic Communications 76, no. 7 (2020): 1143–45. http://dx.doi.org/10.1107/s2056989020008403.

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The title compound, C10H9F3O3, represents the structure of racemic Mosher's Acid (systematic name: 3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid), a carboxylic acid that when resolved can be employed as a chiral derivatizing agent. The compound contains a carboxylic acid group, a methoxy group and a trifluoromethyl substituent on an asymmetric benzylic carbon atom. The two independent molecules in the asymmetric unit form a non-centrosymmetric homochiral dimer via intermolecularly hydrogen-bonded head-to-tail dimers with graph-set notation R 2 2(8) and donor–acceptor hydrogen-bonding distan
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26

Londhe, A. V., B. Gupta, S. Kohli, P. Pardasani, and R. T. Pardasani. "Synthesis, Semiempirical, Stereoselectivity and Pharmacological Activity of a New Class of Spiro Pyrrolidine and Isoquinoline Derivatives." Zeitschrift für Naturforschung B 61, no. 2 (2006): 213–20. http://dx.doi.org/10.1515/znb-2006-0217.

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Abstract1,3-Dipolar cycloaddition of azomethine ylides derived from acenaphthylene-1,2-dione and 5- methyl-benzo[b]-thiophene-2,3-dione with L-proline, thiazolidine-4-carboxylic acid and 1,2,3,4- tetrahydroisoquinoline-3-carboxylic acid with various electron deficient dipolarophiles leads to the formation of novel spiroheterocycles having two or more chiral centers. Semiempirical studies have been performed to understand the stereochemical course of the reaction. The synthesized cycloadducts have been screened for antimicrobial and toxicological activity.
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27

He, Chuan, Bing Zu, Yonghong Guo, and Jie Ke. "Transient- and Native-Directing-Group-Enabled Enantioselective C–H Functionalization." Synthesis 53, no. 12 (2021): 2029–42. http://dx.doi.org/10.1055/a-1372-6627.

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AbstractIn recent years, transition-metal-catalyzed enantioselective C–H bond functionalization using chiral transient directing groups (cTDGs) or native directing groups (NDGs) has emerged as a powerful and attractive­ synthetic approach to streamline the synthesis of chiral molecules­. This short review focuses on recent advances on imine-based cTDGs strategies and native amine and carboxylic acid directed strategies for the asymmetric functionalization of various C–H bonds. We have endeavored to highlight the great potential of this methodology and hope that this review will inspire further
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28

Nishida, Yoshihiro, Masayuki Abe, Hiroshi Ohrui, and Hiroshi Meguro. "(+)-Tert-butyl-1,3-benzodioxole-4-carboxylic acid: Fluorescent chiral carboxylic acid with a 1,3-benzodioxole skeleton." Tetrahedron: Asymmetry 4, no. 7 (1993): 1431–34. http://dx.doi.org/10.1016/s0957-4166(00)80333-x.

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29

Rane, Vipul P., Vinod K. Ahirrao, Kiran B. More, and Ravindra D. Yeole. "Enantiomeric Separation and Thermodynamic Investigation of (R)-N-Tert-Butoxy Carbonyl-Piperidine-3-Carboxylic Acid Hydrazide, a Key Starting Material of Zidebactam." Journal of Chromatographic Science 59, no. 5 (2021): 452–57. http://dx.doi.org/10.1093/chromsci/bmaa141.

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Abstract A new selective, accurate and precise chiral high-performance liquid chromatography method for the separation of (R)-N-tert-butoxy carbonyl-piperidine-3-carboxylic acid hydrazide (RE) and its enantiomer was developed. RE is a key starting material of novel β-lactam enhancer drug Zidebactam. Chiral resolution of more than 10 was achieved on Chiralpak IA column using mobile phase consisting of n-hexane, ethanol in the ratio of 70:30, v/v. The flow rate of the mobile phase was 1.0 mL min−1 and the column oven temperature was 30°C. Detection was carried out at 225 nm. The developed method
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30

Nubbemeyer, Udo, Analuisa Nava, Lukas Trippe, Andrea Frank, Lars Andernach, and Till Opatz. "Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4." Synlett 32, no. 01 (2020): 45–50. http://dx.doi.org/10.1055/s-0040-1707282.

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AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-ca
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31

Cirbes, Cady, and Joseph M. Tanski. "Crystallographic and spectroscopic characterization of (R)-O-acetylmandelic acid." Acta Crystallographica Section E Crystallographic Communications 72, no. 7 (2016): 901–3. http://dx.doi.org/10.1107/s2056989016008653.

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The title compound [systematic name: (R)-(−)-2-acetoxy-2-phenylacetic acid], C10H10O4, is a resolved chiral ester derivative of mandelic acid. The compound contains an acetate group and a carboxylic acid group, which engage in intermolecular hydrogen bonding, forming chains extending parallel to [001] with a short donor–acceptor hydrogen-bonding distance of 2.676 (2) Å.
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32

Poremba, Kelsey E., Victoria A. Lee та Bianca R. Sculimbrene. "Synthesis of α-chiral-β,γ-unsaturated carboxylic acid derivatives using chiral auxiliaries". Tetrahedron 70, № 35 (2014): 5463–67. http://dx.doi.org/10.1016/j.tet.2014.06.116.

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33

Xu, Jing, Xuebo Zhang, Zhongxiang Chen, Zhaofeng Sun, Guangling Bian та Ling Song. "Facile access to chiral β-homoglutamic acid from 3-cyclohexene-carboxylic acid". Synthetic Communications 50, № 22 (2020): 3475–80. http://dx.doi.org/10.1080/00397911.2020.1802760.

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34

Wang, Xueyang, Jianan Wang, Fengbo Ma, Qinghua Bian, Min Wang, and Jiangchun Zhong. "Asymmetric Synthesis of Contact Sex Pheromone of Tetropium fuscum and Its Enantiomer." Molecules 27, no. 20 (2022): 6897. http://dx.doi.org/10.3390/molecules27206897.

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Tetropium fuscum is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (S)-11-methyl-heptacosane, and its enantiomer were synthesized via Evans’ chiral auxiliaries. The key steps of this approach included acylation of carboxylic acid, diastereoselective methylation of oxazolidinone amide, and Wittig coupling of the aldehyde with chiral phosphonium salt. The synthetic pheromones would have potential utility in the control of this pest.
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35

Shen, Cong, Yuhang Zhu, Wenzhou Shen, et al. "Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C–H alkenylations." Organic Chemistry Frontiers 9, no. 8 (2022): 2109–15. http://dx.doi.org/10.1039/d2qo00161f.

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An enantioselective olefinic C–H alkenylation using transient group was disclosed to afford axially chiral aryl 1,3-dienes in up to 99% yields and up to &gt;99% ee. The derived carboxylic acid was efficient ligand in asymmetric C–H alkylation.
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36

Schwendenwein, Daniel, Anna K. Ressmann, Marcello Entner, Viktor Savic, Margit Winkler, and Florian Rudroff. "Chemo-Enzymatic Cascade for the Generation of Fragrance Aldehydes." Catalysts 11, no. 8 (2021): 932. http://dx.doi.org/10.3390/catal11080932.

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In this study, we present the synthesis of chiral fragrance aldehydes, which was tackled by a combination of chemo-catalysis and a multi-enzymatic in vivo cascade reaction and the development of a highly versatile high-throughput assay for the enzymatic reduction of carboxylic acids. We investigated a biocompatible metal-catalyzed synthesis for the preparation of α or β substituted cinnamic acid derivatives which were fed directly into the biocatalytic system. Subsequently, the target molecules were synthesized by an enzymatic cascade consisting of a carboxylate reduction, followed by the sele
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37

Wang, Xiao Ji, Jian Ting Zhang, Dong Wang Liu, Lin Jun Tang, Jun Min Feng, and Shi Peng Chen. "Study on Synthesis of 2-(1-Tert-Butoxycarbonylamino-2-Methyl-Butyl)-Thiazole-4-Carboxylic Acid Methyl Ester." Advanced Materials Research 634-638 (January 2013): 1099–102. http://dx.doi.org/10.4028/www.scientific.net/amr.634-638.1099.

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2-(1-tert-Butoxycarbonylamino-2-methyl-butyl)-thiazole-4-carboxylic acid methyl ester, the chiral unit containing thiazole of a novel cyclic depsipeptide Lyngbyabellin A which exhibited moderate cytotoxicity against KB and LoVo cells, was synthesized from N-t-Boc-L-isoleucine and L-serrine methyl ester monohydrochloride in overall yield 15% through six steps, including condensation, TBS protection, thionation, deprotection, cyclodehydration and aromatization. The ee value of the title chiral thiazole unit is up to 98％.
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38

Roitman, JN, and RY Wong. "Revised Absolute Configurations of Latifolic Acid and the Pyrrolizidine Alkaloid Latifoline." Australian Journal of Chemistry 41, no. 11 (1988): 1781. http://dx.doi.org/10.1071/ch9881781.

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The absolute stereochemistry of (+)- latifolk acid has been determined by single-crystal X-ray crystallographic analysis to be (2S,3R,4R)-3- hydroxy-2,4-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid. The configuration of the three chiral centres is opposite to that presently recorded in the literature. Accordingly, the configuration of the pyrrolizidine alkaloid, latifoline, which includes a latifolic acid side chain, must be revised.
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39

Langer, Thomas, Michael Illich, and Günter Helmchen. "Diastereoselective oxidative coupling of enolates of chiral carboxylic acid derivatives." Tetrahedron Letters 36, no. 25 (1995): 4409–12. http://dx.doi.org/10.1016/0040-4039(95)00786-c.

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40

NISHIDA, Y., M. ABE, H. OHRUI, and H. MEGURO. "ChemInform Abstract: (+)-tert-Butyl-1,3-benzodioxole-4-carboxylic Acid: Fluorescent Chiral Carboxylic Acid with a 1,3-Benzodioxole Skeleton." ChemInform 24, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199347058.

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41

Hayama, Noboru, Yusuke Kobayashi, Eriko Sekimoto та ін. "A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst". Chemical Science 11, № 21 (2020): 5572–76. http://dx.doi.org/10.1039/d0sc01729a.

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42

Chrzanowska, Maria, Agnieszka Grajewska, and Maria D. Rozwadowska. "Diastereoselective Synthesis of (–)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid via Morpholinone Derivatives." Molecules 28, no. 7 (2023): 3200. http://dx.doi.org/10.3390/molecules28073200.

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A simple and convenient synthesis of (–)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid is described, applying a combination of two synthetic methods: the Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization. The diastereomeric morpholinone derivative N-(2,2-diethoxyethyl)-3-(3,4-dimethoxyphenyl)-5-phenyl-1,4-oxazin-2-one formed in the Petasis reaction was further transformed into 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid via Pomeranz–Fritsch–Bobbitt cyclization, a classical method of synthesis leading to the tetrahydroisoquinoline core. We review important examples
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43

Kricheldorf, Hans R., and Andreas Gerken. "New Polymer Syntheses 87. Thermosetting Nematic or Cholesteric Diesters Having Propargyl Endgroups." High Performance Polymers 9, no. 2 (1997): 75–90. http://dx.doi.org/10.1088/0954-0083/9/2/001.

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4-Propargyloxy benzoic acid, 6-propargyloxy-2-naphthoic acid and 4′-propargyloxybiphenyl-4-carboxylic acid were synthesized from the corresponding hydroxy acids and converted into the acid chlorides. Diesters were then prepared by the reaction of these acid chlorides with diphenols such as hydroquinone, methylhydroquinone n-octylthiohydroquinone and phenylhydroquinone. Most of these diesters form an enantiotropic nematic melt but some diesters form a monotropic liquid crystal phase. Cholesteric phases were observed for diesters of ( S)-2-methylbutylthiohydroquinone. Diesters derived from 6-pro
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44

Zhou, Xin, Baiyi Mao, and Zhanbin Zhang. "Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines." Molecules 26, no. 4 (2021): 857. http://dx.doi.org/10.3390/molecules26040857.

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Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)2 was found to be the most effective.
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45

Munusamy, Sathish Kumar, Krishnan Thirumoorthy, Vivek Panyam Muralidharan, Umamahesh Balijapalli, and Sathiyanarayanan Kulathu Iyer. "Enantioselective fluorescent sensing of chiral carboxylic acid by engaging boronic acid and BINOL." Sensors and Actuators B: Chemical 244 (June 2017): 175–81. http://dx.doi.org/10.1016/j.snb.2016.12.099.

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46

García-González, Ángel, Leland Belda, Alejandro Manchado, Carlos T. Nieto, and Narciso Martín Garrido. "(R)-N-Benzyl-N-(1-phenylethyl)cyclohexanamine." Molbank 2023, no. 1 (2023): M1561. http://dx.doi.org/10.3390/m1561.

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The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N-(α-methylbenzyl)amide to methyl cyclohex-1-en-carboxilate obtaining the β-amino ester, followed by carboxylic acid hydrolysis and subsequent Barton descarboxylation. Interestingly, it is a general synthetic procedure of a wide range of chiral amines by careful choice of insaturated esters and alkylation of the ch
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47

Kowalska, Ewelina, Lesław Sieroń, and Anna Albrecht. "Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids." Molecules 27, no. 20 (2022): 6809. http://dx.doi.org/10.3390/molecules27206809.

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Herein, we describe the synthesis of a variety of chiral hybrid pyrrolidine-chromanone polycyclic derivatives. A convenient (3+2)-annulation of azomethine ylides with chromone-3-carboxylic acid realized under Brønsted base catalysis produced highly functionalized products in high yields with good stereoselectivities through asymmetric, intermolecular, and decarboxylative (3+2)-cyclization.
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48

Csuk, René, Anja Kern, and Kristina Mohr. "Synthesis and HPLC-Analysis of N-(2-Phenyl-cyclopropyl)-Substituted Chain Elongated Nucleoside Analogues." Zeitschrift für Naturforschung B 54, no. 11 (1999): 1463–68. http://dx.doi.org/10.1515/znb-1999-1120.

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A novel class of nucleoside analogues containing adenine, uracil, thymine and 5-fluorouracil as the heterocyclic moieties have been prepared from 2-phenylcyclopropane carboxylic acid. These compounds showed weak antitum or activity. The resolution of the racemates on an analytical and semipreparative scale was performed by HPLC using chiral stationary phases.
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49

Jadhav, Sushilkumar. "Synthesis of fluorescent carboxylic acid ligands for construction of monolayers on nanostructures." Open Chemistry 10, no. 5 (2012): 1640–46. http://dx.doi.org/10.2478/s11532-012-0078-2.

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AbstractTwo new long-chain carboxylic acids (1, 2) bearing strong fluorescent group pyrene as ligands for Self-Assembled Monolayers (SAMs) have been synthesized. The multistep targeted synthesis is accomplished by use of Pyren-1-yl methylamine hydrochloride and employing simplified synthetic protocols. Compound 2 contains a chiral center purposely introduced along the atom chain in order to make it suitable for chiro-optical studies of the resulting SAMs.
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50

Poremba, Kelsey E., Victoria A. Lee та Bianca R. Sculimbrene. "ChemInform Abstract: Synthesis of α-Chiral-β,γ-Unsaturated Carboxylic Acid Derivatives Using Chiral Auxiliaries." ChemInform 46, № 4 (2015): no. http://dx.doi.org/10.1002/chin.201504047.

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