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Journal articles on the topic 'Quaternary carbon'

Author: Grafiati

Published: 4 June 2021

Last updated: 27 April 2022

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1

Li, Bi-Jie, and Xin Sun. "Acyclic Quaternary Carbon Stereocenters through Transition-Metal-Catalyzed Enantioselective Functionalization of Unsaturated Hydrocarbons." Synthesis 54, no. 09 (2022): 2103–18. http://dx.doi.org/10.1055/s-0040-1719899.

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AbstractAcyclic quaternary carbon stereocenters occur frequently in natural products, bioactive molecules, and pharmaceutical compounds. Construction of a carbon stereogenic center attached to four different carbons with defined spatial arrangement is a daunting challenge in asymmetric catalysis. Significant efforts have been directed towards the stereoselective construction of such acyclic quaternary carbon stereocenters. In particular, catalytic generation of acyclic quaternary carbon stereocenters through functionalization of unsaturated hydrocarbons is an extremely attractive approach beca

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2

Gutman, Ivan, Dusica Vidovic, and Dragan Stevanovic. "Chemical applications of the Laplacian spectrum. VI On the largest Laplacian eigenvalue of alkanes." Journal of the Serbian Chemical Society 67, no. 6 (2002): 407–13. http://dx.doi.org/10.2298/jsc0206407g.

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The largest Lapacian eigenvalue ?1 of the molecular graph is a quantity important in the theory of the photoelectron spectra of saturated hydrocarbons. It is shown that in the case of alkanes, the presence or absence of quaternary carbon atoms is the main structural feature on which ?1 depends. Within sets of all alkanes with a given number of carbon atoms the species (with and without quaternary carbons atoms) whose ?1-values are minimal and maximal are determined.

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3

Palao, Eduardo, Enol López, Iván Torres-Moya, Antonio de la Hoz, Ángel Díaz-Ortiz, and Jesús Alcázar. "Formation of quaternary carbons through cobalt-catalyzed C(sp3)–C(sp3) Negishi cross-coupling." Chemical Communications 56, no. 59 (2020): 8210–13. http://dx.doi.org/10.1039/d0cc02734k.

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4

Yanagita, Hiroshi, Kazuhiro Kodama, and Shuji Kanemasa. "Double catalytic enantioselective Michael addition reactions of tertiary nucleophile precursors—tertiary/quaternary and quaternary/quaternary carbon–carbon bond formations." Tetrahedron Letters 47, no. 52 (2006): 9353–57. http://dx.doi.org/10.1016/j.tetlet.2006.10.089.

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5

Kita, Yasuyuki, and Hiromichi Fujioka. "Enantioselective constructions of quaternary carbons and their application to the asymmetric total syntheses of fredericamycin A and discorhabdin A." Pure and Applied Chemistry 79, no. 4 (2007): 701–13. http://dx.doi.org/10.1351/pac200779040701.

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An efficient enantioselective construction of quaternary carbons including spiro carbons is an area of intense interest due to the importance of these units as components of biologically active natural products. Prominent methods are presented for the synthesis of chiral, nonracemic quaternary carbon centers by (i) stereospecific rearrangement of optically active epoxides, (ii) enzyme-catalyzed resolution, and (iii) hypervalent iodine reagent-induced ipso-substitution of para-substituted phenol derivatives. These methods were applied to the total syntheses of fredericamycin A and discorhabdin

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6

Fuji, Kaoru. "Asymmetric creation of quaternary carbon centers." Chemical Reviews 93, no. 6 (1993): 2037–66. http://dx.doi.org/10.1021/cr00022a005.

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7

Hayashi, T., R. Shintani, and W. L. Duan. "Asymmetric Construction of Quaternary Carbon Stereocenters." Synfacts 2006, no. 8 (2006): 0821. http://dx.doi.org/10.1055/s-2006-942013.

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8

Davies, Stephen G., and Jonathan C. Walker. "Stereoselective synthesis of quaternary carbon centres." Journal of the Chemical Society, Chemical Communications, no. 6 (1986): 495. http://dx.doi.org/10.1039/c39860000495.

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9

Lanke, Veeranjaneyulu, and Ilan Marek. "Nucleophilic Substitution at Quaternary Carbon Stereocenters." Journal of the American Chemical Society 142, no. 12 (2020): 5543–48. http://dx.doi.org/10.1021/jacs.0c01133.

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10

Shintani, R., T. Hayashi, Y. Tsutsumi, M. Nagaosa, and T. Nishimura. "Synthesis of All-Carbon Quaternary Stereocenters." Synfacts 2009, no. 12 (2009): 1376. http://dx.doi.org/10.1055/s-0029-1218255.

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11

Stoltz, Brian, Samantha Shockley, and J. Hethcox. "Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account." Synlett 29, no. 19 (2018): 2481–92. http://dx.doi.org/10.1055/s-0037-1610217.

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Our lab has long been interested in the development of methods for the creation of enantioenriched all-carbon quaternary stereocenters. Historically, our interest has centered on palladium-catalyzed allylic alkylation, though recent efforts have moved to include the study of iridium catalysts. Whereas palladium catalysts enable the preparation of isolated stereocenters, the use of iridium catalysts allows for the direct construction of vicinal stereocenters via an enantio-, diastereo-, and regioselective allylic alkylation. This Account details the evolution of our research program from incept

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12

Liu, Yiyang, Marc Liniger, Ryan M. McFadden, et al. "Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation." Beilstein Journal of Organic Chemistry 10 (October 28, 2014): 2501–12. http://dx.doi.org/10.3762/bjoc.10.261.

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Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a c

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13

Chiang, Yu-Chun, Wei-Ting Chin, and Chih-Cheng Huang. "The Application of Hollow Carbon Nanofibers Prepared by Electrospinning to Carbon Dioxide Capture." Polymers 13, no. 19 (2021): 3275. http://dx.doi.org/10.3390/polym13193275.

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Coaxial electrospinning has been considered a straightforward and convenient method for producing hollow nanofibers. Therefore, the objective of this study was to develop hollow activated carbon nanofibers (HACNFs) for CO2 capture in order to reduce emissions of CO2 to the atmosphere and mitigate global warming. Results showed that the sacrificing core could be decomposed at carbonization temperatures above 900 °C, allowing the formation of hollow nanofibers. The average outer diameters of HACNFs ranged from 550 to 750 nm, with a shell thickness of 75 nm. During the carbonization stage, the de

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14

Kessler, H., W. Bermel, and C. Griesinger. "Determination of carbon-carbon connectivities, assignment of quaternary carbons, and extraction of carbon-carbon coupling constants by carbon-relayed hydrogen-carbon spectroscopy." Journal of Magnetic Resonance (1969) 62, no. 3 (1985): 573–79. http://dx.doi.org/10.1016/0022-2364(85)90231-8.

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15

Striegl, Robert G., and David E. Armstrong. "Carbon dioxide retention and carbon exchange on unsaturated Quaternary sediments." Geochimica et Cosmochimica Acta 54, no. 8 (1990): 2277–83. http://dx.doi.org/10.1016/0016-7037(90)90051-l.

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16

Hossain, M. Mahmun, Eduardo Alberch, Nazim Uddin та Maria Shevyrev. "Synthesis of α-aryl quaternary carbon centers". Arkivoc 2010, № 4 (2011): 139–46. http://dx.doi.org/10.3998/ark.5550190.0011.412.

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17

Sun, X., K. Frimpong, and K. L. Tan. "Synthesis of Quaternary Carbon Centers via Hydroformylation." Journal of the American Chemical Society 132, no. 34 (2010): 11841–43. http://dx.doi.org/10.1021/ja1036226.

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18

Quasdorf, Kyle W., and Larry E. Overman. "Catalytic enantioselective synthesis of quaternary carbon stereocentres." Nature 516, no. 7530 (2014): 181–91. http://dx.doi.org/10.1038/nature14007.

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19

Sundquist, Eric T. "The Global Carbon Cycle and Quaternary Paleoclimates." Episodes 10, no. 1 (1987): 7–10. http://dx.doi.org/10.18814/epiiugs/1987/v10i1/004.

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20

Kummer, David A., William J. Chain, Marvin R. Morales, Olga Quiroga, and Andrew G. Myers. "Stereocontrolled Alkylative Construction of Quaternary Carbon Centers." Journal of the American Chemical Society 130, no. 40 (2008): 13231–33. http://dx.doi.org/10.1021/ja806021y.

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21

Xie, Weiqing, Jiadong Hu, and Xin Yu. "New Strategy for Forging Contiguous Quaternary Carbon Centers via H2O2-Mediated Ring Contraction." Synlett 28, no. 19 (2017): 2517–24. http://dx.doi.org/10.1055/s-0036-1590979.

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Stereospecific construction of contiguous quaternary carbon centers constitutes a major challenge in natural product synthesis. A general protocol that enables stereospecific construction of all stereoisomers of such a moiety remains elusive. In this article, we will discuss the oxidative ring contraction of all-substituted cyclic α-formyl ketones mediated by H2O2, which provides a facile access to the stereospecific construction of contiguous quaternary carbon centers.

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22

Zhou, Feng, Lei Zhu, Bo-Wen Pan, Yang Shi, Yun-Lin Liu, and Jian Zhou. "Catalytic enantioselective construction of vicinal quaternary carbon stereocenters." Chemical Science 11, no. 35 (2020): 9341–65. http://dx.doi.org/10.1039/d0sc03249b.

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This review summarizes the advances in catalytic enantioselective construction of vicinal quaternary carbon stereocenters, introduces major synthetic strategies and discusses their advantages and limitations, and outlines the synthetic opportunities.

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23

Chaiwan, Pattarakamon, and Jantrawan Pumchusak. "The Synergistic Effects of Multi-Filler Addition on the Mechanical and Thermo-Mechanical Properties of Phenolic Resins." Materials Science Forum 940 (December 2018): 23–27. http://dx.doi.org/10.4028/www.scientific.net/msf.940.23.

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The effects of the carbon fiber (CF), carbon black (CB) and nanosilica (SiO2) on the mechanical properties of the phenolic resin (PF) were studied and the optimum composition was selected for the preparation of quaternary composites (CF/CB/SiO2 phenolic composites). The incorporation of poly (acrylonitrile-co-butadiene) rubber (NBR) to strengthen the quaternary composites were also studied. The morphological, mechanical and thermo-mechanical properties of unmodified and NBR modified-quaternary phenolic composites were investigated. The phenolic compounds were mixed by ball milling and the phen

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24

Wang, Zhuo, and Junyang Liu. "All-carbon [3 + 2] cycloaddition in natural product synthesis." Beilstein Journal of Organic Chemistry 16 (December 9, 2020): 3015–31. http://dx.doi.org/10.3762/bjoc.16.251.

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Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-car

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25

He, Chonglong, Yipeng Zhou, Zhanhuan Li, Jianfeng Xu та Xingkuan Chen. "N-Heterocyclic carbene catalyzed asymmetric [3 + 3] cycloaddtion of β,β-disubstituted, α,β-unsaturated carboxylic esters with 3-aminobenzofurans". Organic Chemistry Frontiers 8, № 7 (2021): 1569–74. http://dx.doi.org/10.1039/d0qo01489c.

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26

Wen, Kai-Ge, Yi-Yuan Peng, and Xing-Ping Zeng. "Advances in the catalytic asymmetric synthesis of quaternary carbon containing cyclobutanes." Organic Chemistry Frontiers 7, no. 17 (2020): 2576–97. http://dx.doi.org/10.1039/d0qo00685h.

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27

Chen, Long. "Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters." Synthesis 50, no. 03 (2017): 440–69. http://dx.doi.org/10.1055/s-0036-1590958.

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Phosphorus-substituted quaternary carbon stereocenters exist widely in drugs and biologically active compounds. Catalytic asymmetric synthesis of such quaternary carbon stereogenic centers is of significant importance, with four synthetic strategies being established. This review summarizes the recent progress in this field, including the advantages and limitations of each strategy, briefly discusses the reaction mechanisms and challenges, and outlines synthetic opportunities still open.1 Introduction2 Asymmetric Hydrophosphonylation3 Asymmetric Electrophilic Phosphination4 Asymmetric Function

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28

Majetich, George, and Jing Fang. "The synthesis of quaternary carbon centers through cyclialkylations." Tetrahedron Letters 39, no. 46 (1998): 8381–84. http://dx.doi.org/10.1016/s0040-4039(98)01931-5.

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29

Pearson, Anthony J., and Vikram D. Khetani. "Construction of quaternary carbon centers using organomolybdenum chemistry." Journal of the American Chemical Society 111, no. 17 (1989): 6778–89. http://dx.doi.org/10.1021/ja00199a043.

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30

Xu, Peng-Wei, Jin-Sheng Yu, Chen Chen, Zhong-Yan Cao, Feng Zhou, and Jian Zhou. "Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters." ACS Catalysis 9, no. 3 (2019): 1820–82. http://dx.doi.org/10.1021/acscatal.8b03694.

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31

Schaus, A., A. Ting, and S. Lou. "Quaternary Carbon Centers by Cinchonine-Catalyzed Mannich Reactions." Synfacts 2006, no. 7 (2006): 0729. http://dx.doi.org/10.1055/s-2006-941913.

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32

RajanBabu, T., and A. Zhang. "All-Carbon Quaternary Centers via Catalytic Asymmetric Hydrovinylation." Synfacts 2006, no. 8 (2006): 0800. http://dx.doi.org/10.1055/s-2006-942014.

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33

FUJI, K. "ChemInform Abstract: Asymmetric Creation of Quaternary Carbon Centers." ChemInform 25, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199403291.

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34

Lanke, Veeranjaneyulu, and Ilan Marek. "Correction to “Nucleophilic Substitution at Quaternary Carbon Stereocenters”." Journal of the American Chemical Society 142, no. 16 (2020): 7710–12. http://dx.doi.org/10.1021/jacs.0c03380.

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35

Trost, Barry M., and Chunhui Jiang. "Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters." Synthesis, no. 3 (2006): 369–96. http://dx.doi.org/10.1055/s-2006-926302.

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36

Quiclet-Sire, Béatrice, and Samir Z. Zard. "The xanthate route to all-carbon quaternary centers." Science China Chemistry 62, no. 11 (2019): 1450–62. http://dx.doi.org/10.1007/s11426-019-9587-x.

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37

Wang, Bo, An-Jun Deng, Zhi-Hong Li, Nan Wang, and Hai-Lin Qin. "Syntheses and Structure–Activity Relationships in Growth Inhibition Activity against Human Cancer Cell Lines of 12 Substituted Berberine Derivatives." Molecules 25, no. 8 (2020): 1871. http://dx.doi.org/10.3390/molecules25081871.

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In this study, quaternary berberine chloride is used as a lead compound to design and synthesize a series of berberine-12-amine derivatives to evaluate the growth inhibition activity against human cancer cell lines. Forty-two compounds of several series were obtained. The quaternary berberine-12-N,N-di-n-alkylamine chlorides showed the targeted activities with the IC50 values of most active compounds being dozens of times those of the positive control. A significant structure–activity relationship (SAR) was observed. The activities of quaternary berberine-12-N,N-di-n-alkylamine chlorides are s

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38

Li, Minghua, Nan Ji, Ting Lan, Wei He та Rui Liu. "Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates". RSC Adv. 4, № 39 (2014): 20346–50. http://dx.doi.org/10.1039/c4ra01390e.

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The catalytic enantioselective aza-Henry reaction of N-Boc aldimines 2 and 2-nitropropionic acid ethyl ester 3 in mixed solvents were catalyzed by cinchona quaternary ammonium salts to form a new quaternary carbon center. High yields (up to 90%), excellent enantioselectivities (up to 99% ee) and diastereoselectivities ratio (up to 22 : 1) were successfully obtained with mild conditions.

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39

Liu, Danyang, Zhijian Zhou, and Hao Liu. "The Theoretical Total Synthesis of an Aromatic Esters of the Crinane Amaryllidaceae Alkaloid Ambelline." E3S Web of Conferences 267 (2021): 02011. http://dx.doi.org/10.1051/e3sconf/202126702011.

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ABSTRACT. A series of crinane-type alkaloid ambelline derivatives were assessed for their potency to inhibit both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), which has been shown to be effective medicine for the treatment of Alzheimer’s disease. However, no enzyme modification has been reported total synthesis. In this work, two possible theoretical synthesis paths of Crinane-type alkaloid ambelline were discussed in this article. The major difficulty of the proposed synthesis was the synthesis of the quaternary carbon. One of the approaches emphasized on the reactions betwe

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40

Sato, Ryota, Ryuji Okamoto, Takumi Ishizuka, Atsushi Nakayama, Sangita Karanjit, and Kosuke Namba. "Microwave-assisted Tertiary Carbon Radical Reaction for Construction of Quaternary Carbon Center." Chemistry Letters 48, no. 5 (2019): 414–17. http://dx.doi.org/10.1246/cl.190040.

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41

Li, Jun-Long, Qing-Zhu Li, Yue Liu, and Hai-Jun Leng. "Asymmetric Construction of Halogenated Cyclic Quaternary Carbon Center through Enolate Activation of Aldehydes." Synlett 29, no. 20 (2018): 2601–7. http://dx.doi.org/10.1055/s-0037-1610256.

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The construction of a chiral halogenated cyclic quaternary carbon center through various catalytic strategies is an emerging hot topic in the field of asymmetric synthesis. Herein, we give a summary of recently developed synthetic methods for preparing such structures. In addition, a novel enolate activation mode of aldehydes is highlighted, which provides an elegant pathway to access enantiopure heterocycles featuring a halogenated quaternary stereocenter through organocatalytic [4+2] cycloaddition.

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42

Butora, Gabriel, Ludvík Bláha, Miroslav Rajšner, and Ivan Helfert. "Some New Analogues of Verapamil and Mepamil. Synthesis and Basic Pharmacological Properties." Collection of Czechoslovak Chemical Communications 57, no. 9 (1992): 1967–81. http://dx.doi.org/10.1135/cccc19921967.

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Some new analogues of verapamil (Ia) and mepamil (Ib), calcium antagonists of arylalkylamine type, were synthesized and screened for cardiovascular activities. The basic structure was modified a) on the phenyl ring, attached to the quaternary carbon, b) on the alkyl group, attached to the quaternary carbon and c) on the alkylamino group, attached in position 3 to the n-propyl fragment. Except of 2-(2-chlorophenyl)-2-isopropyl-5-(N-methylhomoveratrylamino)valeronitrile (VIa), all the synthesized compounds exhibited lower hypotensive activity, than the mother compound, verapamil.

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43

Wu, Xin-Xing, Hui Tian, Yu Wang, et al. "A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process." Organic Chemistry Frontiers 5, no. 22 (2018): 3310–14. http://dx.doi.org/10.1039/c8qo00964c.

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44

Prahas, Devarly, M. J. Wang, Suryadi Ismadji, and J. C. Liu. "Enhanced adsorption of quaternary amine using modified activated carbon." Water Science and Technology 69, no. 10 (2014): 2085–92. http://dx.doi.org/10.2166/wst.2014.085.

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This study examined different methodologies to modify activated carbon (AC) for the removal of quaternary amine, tetramethylammonium hydroxide (TMAH), from water. Commercial carbon (WAC) was treated by nitric acid oxidation (NA-WAC), silica impregnation (SM-WAC0.5), and oxygen plasma (P10-WAC), and their characteristics and adsorption capacity were compared. The Langmuir model fitted the equilibrium adsorption data well under different pH. The maximum adsorption capacity of WAC was 27.77 mg/g, while those of NA-WAC, SM-WAC 0.5, and P10-WAC were 37.46, 32.83 and 29.03 mg/g, respectively. Nitric

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45

Morais, Rafael Gomes, Natalia Rey-Raap, José Luís Figueiredo, and Manuel Fernando Ribeiro Pereira. "Glucose-derived carbon materials with tailored properties as electrocatalysts for the oxygen reduction reaction." Beilstein Journal of Nanotechnology 10 (May 21, 2019): 1089–102. http://dx.doi.org/10.3762/bjnano.10.109.

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Nitrogen-doped biomass-derived carbon materials were prepared by hydrothermal carbonization of glucose, and their textural and chemical properties were subsequently tailored to achieve materials with enhanced electrochemical performance towards the oxygen reduction reaction. Carbonization and physical activation were applied to modify the textural properties, while nitrogen functionalities were incorporated via different N-doping methodologies (ball milling and conventional methods) using melamine. A direct relationship between the microporosity of the activated carbons and the limiting curren

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46

Huang, Yubing, Xianwei Li, Xu Wang, et al. "Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center." Chemical Science 8, no. 10 (2017): 7047–51. http://dx.doi.org/10.1039/c7sc02867a.

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47

Lanke, Veeranjaneyulu, and Ilan Marek. "Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres." Chemical Science 11, no. 35 (2020): 9378–85. http://dx.doi.org/10.1039/d0sc02562c.

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48

Xue, Weichao, Xiao Jia, Xuan Wang, Xianghua Tao, Zhigang Yin, and Hegui Gong. "Nickel-catalyzed formation of quaternary carbon centers using tertiary alkyl electrophiles." Chemical Society Reviews 50, no. 6 (2021): 4162–84. http://dx.doi.org/10.1039/d0cs01107j.

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49

Zhang, Qingqing, Jinghua Huang, Feinan Hu, et al. "The distribution of organic carbon fractions in a typical loess-paleosol profile and its paleoenvironmental significance." PeerJ 6 (April 13, 2018): e4611. http://dx.doi.org/10.7717/peerj.4611.

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Background The loess-paleosol sequence on the Loess Plateau has been considered an important paleoclimatic archive to study global climatic and environmental changes in the Quaternary. So far, little attention has been paid to the characteristics of soil organic carbon fractions in loess-paleosol sequences, which may provide valuable information for exploring the evolution of climate and environment in the Quaternary on the Loess Plateau. Methods In order to explore the significance of mineral-associated organic carbon to total organic carbon (MOC/TOC) ratios in the loess-paleosol sequence for

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50

Long, Rong, Jun Huang, Jianxian Gong, and Zhen Yang. "Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis." Natural Product Reports 32, no. 11 (2015): 1584–601. http://dx.doi.org/10.1039/c5np00046g.

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