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Artykuły w czasopismach na temat „Regioselective reduction”

Autor: Grafiati

Data publikacji: 23 listopada 2024

Data aktualizacji: 31 lipca 2025

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1

Butler, Christopher R., Justin Bendesky, and Allen Milton Schoffstall. "Regioselective Reduction of 1H-1,2,3-Triazole Diesters." Molecules 26, no. 18 (2021): 5589. http://dx.doi.org/10.3390/molecules26185589.

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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was at

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2

Hussaini, Syed Raziullah, та Mark G. Moloney. "Regioselective Reduction of β‐Enaminoesters". Synthetic Communications 35, № 8 (2005): 1129–34. http://dx.doi.org/10.1081/scc-200054223.

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3

Hirota, Kosaku, Hironao Sajiki, Ryuji Hattori, Yasunari Monguchi, Genzoh Tanabe, and Osamu Muraoka. "Regioselective BH3–hydride reduction of inosine derivatives." Tetrahedron Letters 43, no. 4 (2002): 653–55. http://dx.doi.org/10.1016/s0040-4039(01)02209-2.

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4

Bruhn, Torsten, and Christian Brückner. "Origin of the Regioselective Reduction of Chlorins." Journal of Organic Chemistry 80, no. 10 (2015): 4861–68. http://dx.doi.org/10.1021/acs.joc.5b00137.

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5

Setamdideh, Davood, and Behzad Zeynizadeh. "Mild and Convenient Method for Reduction of Carbonyl Compounds with the NaBH4/Charcoal System in Wet THF." Zeitschrift für Naturforschung B 61, no. 10 (2006): 1275–81. http://dx.doi.org/10.1515/znb-2006-1014.

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The NaBH4/C (charcoal) system reduces a variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in high to excellent yields. Reduction reactions were carried out in wet THF at r. t. In addition, regioselective 1,2-reduction of α,β - unsaturated aldehydes and ketones was achieved perfectly with this reducing system. By decreasing the amount of aprotic solvent, all reductions took place fast and efficiently under solid-gel condition

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6

Katagiri, Takayuki, and Yutaka Amao. "Visible light driven selective NADH regeneration using a system of water-soluble zinc porphyrin and homogeneous polymer-dispersed rhodium nanoparticles." New Journal of Chemistry 45, no. 35 (2021): 15748–52. http://dx.doi.org/10.1039/d1nj02856a.

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We discovered the catalytic activity of Rh nanoparticles dispersed by polyvinylpyrrolidone for regioselective NAD+ reduction to 1,4-NADH. Only 1,4-NADH was produced as the reduction product of NAD+ with visible-light irradiation.

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7

Nguyen, Mai, Issam Kherbouche, Sarra Gam-Derouich, et al. "Regioselective surface functionalization of lithographically designed gold nanorods by plasmon-mediated reduction of aryl diazonium salts." Chem. Commun. 53, no. 82 (2017): 11364–67. http://dx.doi.org/10.1039/c7cc05974d.

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8

Tanwar, Babita, Priyank Purohit, Banothu Naga Raju, Dinesh Kumar, Damodara N. Kommi, and Asit K. Chakraborti. "An “all-water” strategy for regiocontrolled synthesis of 2-aryl quinoxalines." RSC Advances 5, no. 16 (2015): 11873–83. http://dx.doi.org/10.1039/c4ra16568c.

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9

Ishii, Hideki, Sergei V. Dzyuba, and Koji Nakanishi. "Lactone-free ginkgolides via regioselective DIBAL-H reduction." Organic & Biomolecular Chemistry 3, no. 19 (2005): 3471. http://dx.doi.org/10.1039/b509129b.

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10

Davey, C. "Regioselective reduction of substituted dinitroarenes using baker's yeast." Tetrahedron Letters 35, no. 41 (1994): 7867–70. http://dx.doi.org/10.1016/s0040-4039(00)77393-x.

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11

Davey, Claire L., Lawson W. Powell, Nicholas J. Turner, and Andrew Wells. "Regioselective reduction of substituted dinitroarenes using baker's yeast." Tetrahedron Letters 35, no. 42 (1994): 7867–70. http://dx.doi.org/10.1016/0040-4039(94)80139-8.

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12

Li, Jide, Weiping Tang, Demin Ren, Jiaxi Xu, and Zhanhui Yang. "Iridium-catalysed highly selective reduction–elimination of steroidal 4-en-3-ones to 3,5-dienes in water." Green Chemistry 21, no. 8 (2019): 2088–94. http://dx.doi.org/10.1039/c9gc00654k.

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13

Stachel, Hans-Dietrich, Josef Schachtner, and Josef Seidel. "Reduktion cyclischer Maleinsäurederivate/Reduction of Cyclic Maleic Acid Derivatives." Zeitschrift für Naturforschung B 51, no. 3 (1996): 409–16. http://dx.doi.org/10.1515/znb-1996-0317.

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Abstract A series of potentially cytotoxic α,β-unsaturated γ -hydroxy-butyrolactones, -lactams and -thiolactones has been synthesized via regioselective hydride reduction of the appropriate maleic acid anhydrides, imides and thioanhydrides. By this means a straightforward access to naturally occurring antibiotic narthigenine 2, its hitherto unknown thio-analogue 5b and higher substituted derivatives and analogues of 2 is presented.

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14

Liu, Hsing-Jang, and Weide Luo. "Synthetic applications of glycidic thiolesters. Regioselective reduction to 1,3-diols and 2,3-epoxy alcohols." Canadian Journal of Chemistry 70, no. 1 (1992): 128–34. http://dx.doi.org/10.1139/v92-022.

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Glycidic thiolesters were shown to undergo regioselective reduction with Raney nickel to give 1,3-diols. With sodium borohydride at room temperature and lithium aluminum hydride at −78 °C, the reduction of glycidic thiolesters was found to proceed chemoselectively to furnish 2,3-epoxy alcohols. Keywords: glycidic thiolesters, reduction, 1,3-diols, 2,3-epoxy alcohols.

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15

Devaux, Jean-François, Steven V. O'Neil, Nathalie Guillo, and Leo A. Paquette. "Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917." Collection of Czechoslovak Chemical Communications 65, no. 4 (2000): 490–510. http://dx.doi.org/10.1135/cccc20000490.

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An enantioselective approach to construction of the complex framework of the CP compounds is presented. The synthesis relies on initial elaboration of the two sidechains. The "upper" appendage was asymmetrically dihydroxylated with both AD-mix reagents in order to lend flexibility to the scheme and provide the necessary handle for evolving the additional stereogenic centers. These fragments were linked to benzoic acid via Birch reduction-alkylation and subsequent cuprate addition. A series of functionalization reactions including dissolving metal reduction, Claisen rearrangement, iodolactoniza

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16

Tan, Minghui, Guohui Yang, Tiejun Wang, et al. "Active and regioselective rhodium catalyst supported on reduced graphene oxide for 1-hexene hydroformylation." Catalysis Science & Technology 6, no. 4 (2016): 1162–72. http://dx.doi.org/10.1039/c5cy01355k.

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17

Tassano, Erika, Kemal Merusic, Isa Buljubasic, et al. "Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer." Chemical Communications 56, no. 47 (2020): 6340–43. http://dx.doi.org/10.1039/d0cc02509g.

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Alcohol dehydrogenases catalyze the regioselective lactonization of dialdehydes via a bio-Tishchenko-like reaction. The nicotinamide-dependent self-sufficient reduction–oxidation sequence proceeds through a formal intramolecular hydride shift.

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18

Gates, Ashley M., and Webster L. Santos. "Regioselective Diboron-Mediated Semireduction of Terminal Allenes." Synthesis 51, no. 24 (2019): 4619–24. http://dx.doi.org/10.1055/s-0039-1690207.

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A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

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19

Cheng, Hsiu-Yi, Chong-Si Sun, and Duen-Ren Hou. "Regioselective Palladium-Catalyzed Formate Reduction ofN-Heterocyclic Allylic Acetates." Journal of Organic Chemistry 72, no. 7 (2007): 2674–77. http://dx.doi.org/10.1021/jo0624896.

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20

Milewska, Maria J., Tomasz Bytner, and Tadeusz Połoński. "Synthesis of Lactams by Regioselective Reduction of Cyclic Dicarboximides." Synthesis 1996, no. 12 (1996): 1485–88. http://dx.doi.org/10.1055/s-1996-4405.

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21

Keglevich, Györg, Zsolt Böcskei, Kálmán Újszászy, and László Tőke. "Synthesis of 1,2,3,6-Tetrahydrophosphorin 1-Oxides by Regioselective Reduction." Synthesis 1997, no. 12 (1997): 1391–93. http://dx.doi.org/10.1055/s-1997-1364.

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22

Denislamova, E. S., N. V. Bubnov, and A. N. Maslivets. "Regioselective reduction of 1H-pyrrole-2,3-diones with thioacetamide." Russian Journal of Organic Chemistry 49, no. 2 (2013): 312. http://dx.doi.org/10.1134/s107042801302022x.

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23

Battisti, Umberto M., Giuseppe Cannazza, Marina M. Carrozzo, et al. "Regioselective reduction of 3-substituted 2,3-dihydrobenzothiadiazines with borohydrides." Tetrahedron Letters 51, no. 33 (2010): 4433–36. http://dx.doi.org/10.1016/j.tetlet.2010.06.081.

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24

Jumde, Varsha R., Niek N. H. M. Eisink, Martin D. Witte, and Adriaan J. Minnaard. "C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction." Journal of Organic Chemistry 81, no. 22 (2016): 11439–43. http://dx.doi.org/10.1021/acs.joc.6b02074.

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25

Nomura, Kota, Tadashi Mizoguchi, and Hitoshi Tamiaki. "Regioselective Reduction Pathway of Geranylgeranyl Moiety in Chlorophyll Biosynthesis." Biophysical Journal 106, no. 2 (2014): 182a—183a. http://dx.doi.org/10.1016/j.bpj.2013.11.1032.

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26

Civitello, Edgar R., and Henry Rapoport. "The regioselective cleavage of aryl tosylates by electrochemical reduction." Journal of Organic Chemistry 57, no. 3 (1992): 834–40. http://dx.doi.org/10.1021/jo00029a010.

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27

Hirota, Kosaku, Hironao Sajiki, Ryuji Hattori, Yasunari Monguchi, Genzoh Tanabe, and Osamu Muraoka. "ChemInform Abstract: Regioselective BH3-Hydride Reduction of Inosine Derivatives." ChemInform 33, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.200216204.

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28

Hagiwara, Hisahiro, Naomi Honma, Kimihiko Kinugawa, Shota Sato, Takashi Hoshi, and Toshio Suzuki. "Second Generation Synthesis of the Neo-Clerodane Diterpenoid Methyl Barbascoate." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800706.

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The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

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29

Kazmia, Syed Najam-ul-Hussain, Zaheer Ahmed, Abdul Malik, Nighat Afza, and Wolfgang Voelterc. "A Regioselective One Pot Synthesis and Synthetic Applications of Cyanodeoxy Sugars by Cyanotrimethylsilane." Zeitschrift für Naturforschung B 50, no. 2 (1995): 294–302. http://dx.doi.org/10.1515/znb-1995-0225.

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The regioselective epoxide opening of different 2,3-anhydropyranoses by cyanotrimethylsilane is investigated. The isolated cyanodeoxy pyranoses allow easy access to the corresponding branched-chains aminomethyl sugars by lithium aluminium hydride reduction or sugar amides by controlled acid hydrolysis.

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30

Liu, Huiyuan, Yujiang Song, Shushuang Li, et al. "Synthesis of core/shell structured Pd3Au@Pt/C with enhanced electrocatalytic activity by regioselective atomic layer deposition combined with a wet chemical method." RSC Advances 6, no. 71 (2016): 66712–20. http://dx.doi.org/10.1039/c6ra04990g.

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Core/shell structured Pd<sub>3</sub>Au@Pt/C created by regioselective atomic layer deposition combined with a wet chemical method demonstrates improved electrocatalytic activity toward formic acid oxidation and oxygen reduction compared with commercial Pt/C.

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31

Ishitsuka, Takuya, Yasuhiro Okuda, Robert K. Szilagyi, Seiji Mori, and Yasushi Nishihara. "The molecular mechanism of palladium-catalysed cyanoesterification of methyl cyanoformate onto norbornene." Dalton Transactions 45, no. 18 (2016): 7786–93. http://dx.doi.org/10.1039/c6dt00341a.

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Density functional theory-based potential energy surface investigation revealed that the reaction mechanism of palladium-catalysed cyanoesterification onto norbornene (NBE) proceeds through exclusive exo-coordination, regioselective olefin insertion first into the Pd–COOR bond, and reduction elimination to form the subsituted NBE.

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32

Wang, Jia-Yin, Guigen Li, Wen-Juan Hao, and Bo Jiang. "Enantio- and Regioselective CuH-Catalyzed Conjugate Reduction of Yne–Allenones." Organic Letters 23, no. 10 (2021): 3828–33. http://dx.doi.org/10.1021/acs.orglett.1c00892.

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33

Zhang, Bing, Xueying Guo, Lei Tao, Ruolin Li, Zhenyang Lin, and Wanxiang Zhao. "Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones." ACS Catalysis 12, no. 8 (2022): 4640–47. http://dx.doi.org/10.1021/acscatal.2c00520.

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34

Nishizawa, Mugio, Hisaya Nishide, Kaoru Kuriyama, and Yuji Hayashi. "Regioselective reduction of .ALPHA.,.GAMMA.-onoceradienedione : Synthesis of lansiolic acid." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 10 (1986): 4443–46. http://dx.doi.org/10.1248/cpb.34.4443.

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35

Hunter, Roger, and Birgit Bartels. "The first solvent-directed regioselective ketal reduction of unsymmetrical glycols." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1991): 2887. http://dx.doi.org/10.1039/p19910002887.

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36

Dragovich, Peter S., Thomas J. Prins, and Ru Zhou. "Palladium Catalyzed, Regioselective Reduction of 1,2-Epoxides by Ammonium Formate." Journal of Organic Chemistry 60, no. 15 (1995): 4922–24. http://dx.doi.org/10.1021/jo00120a042.

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37

Brestensky, Donna M., та Jeffrey M. Stryker. "Regioselective conjugate reduction and reductive silylation of α,β-unsaturated". Tetrahedron Letters 30, № 42 (1989): 5677–80. http://dx.doi.org/10.1016/s0040-4039(00)76168-5.

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38

Dotsenko, V. V., and S. G. Krivokolysko. "Regioselective reduction of 2-cyanoprop-2-enethioamides with sodium borohydride." Russian Chemical Bulletin 61, no. 12 (2012): 2261–64. http://dx.doi.org/10.1007/s11172-012-0321-1.

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39

Nakamura, Kaoru, Shin-ichi Kondo, Yasushi Kawai, Kouichi Hida, Kazutada Kitano та Atsuyoshi Ohno. "Enantio- and regioselective reduction of α-diketones by baker's yeast". Tetrahedron: Asymmetry 7, № 2 (1996): 409–12. http://dx.doi.org/10.1016/0957-4166(96)00020-1.

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40

Epling, Gary A., and Qingxi Wang. "Regioselective reduction of epoxides by electron transfer—a photochemical approach." J. Chem. Soc., Chem. Commun., no. 16 (1992): 1133–34. http://dx.doi.org/10.1039/c39920001133.

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41

Lee, Sun-Hwa, Dmitry V. Gutsulyak, and Georgii I. Nikonov. "Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane." Organometallics 32, no. 16 (2013): 4457–64. http://dx.doi.org/10.1021/om400269q.

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42

Yamaji, Ayaka, Hayato Tsurugi, Yoshihiro Miyake, Kazushi Mashima, and Hiroshi Shinokubo. "Chemo- and Regioselective Reduction of 5,15-Diazaporphyrins Providing Antiaromatic Azaporphyrinoids." Chemistry - A European Journal 22, no. 12 (2016): 3956–61. http://dx.doi.org/10.1002/chem.201600066.

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43

Hosoda, Ryusuke, Yoshiyuki Horio, Kei Shimoda, Manabu Hamada, Hatsuyuki Hamada, and Hiroki Hamada. "Regioselective Hydroxylation and Glucosylation of Flavanones with Cultured Plant Cells of Eucalyptus perriniana." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800712.

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Cultured plant cells of Eucalyptus perriniana catalyzed reduction regioselective hydroxylation and regioselective glycosylation of flavanones. (2 S)-Flavanone was converted into (2 S)-flavan-4-ol (2 S)-flavan-4,7-diol (2 S)-flavan-7-ol (2 S)-flavan-7-yl glucoside and (2 S)-flavan-7-yl gentiobioside. The cells glucosylated (2 S)-flavan-6-ol to (2 S)-flavan-6-yl glucoside. (2 S)-Flavan-2′-ol was transformed to (2 S)-flavan-2′,4-diol (2 S)-flavan-2′,7-diol (2 S)-flavan-2′-yl glucoside. In addition (2 S)-flavan-4′-ol was transformed to (2 S)-flavan-4,4′-diol (2 S)-flavan-4′,7-diol (2 S)-flavan-4′-

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44

Ashikari, Yosuke, Yiyuye Yao, Kyoko Mandai, and Aiichiro Nagaki. "Regioselective Electrocatalytic Deuteration Reactions in PEM Reactor." ECS Meeting Abstracts MA2024-02, no. 53 (2024): 3614. https://doi.org/10.1149/ma2024-02533614mtgabs.

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Although organic chemistry has brought significant benefits to humanity by providing a wide range of chemicals, conventional production methods often generate a significant amount of chemical waste. As the need for sustainability increases, there is a growing demand for organic reactions that utilize fewer chemical reagents, resulting in reduced waste generation. In this context, electrochemical synthetic methods have garnered great attention in recent decades. Unlike general redox reactions in organic synthesis, which require stoichiometric amounts of oxidants and reductants, electrochemical

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45

Liu, Jun, Zhi-Bing Dong, Caizhu Chang, Jialin Geng, Yinxin Liu, and Yuguo Du. "Stereoselective Total Synthesis of Arundinolides A and B." Synthesis 52, no. 10 (2020): 1576–84. http://dx.doi.org/10.1055/s-0039-1691699.

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The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

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46

Zhang, Miaomiao, Hongmei Jiao, Haojie Ma, et al. "Zn-Catalyzed Regioselective and Chemoselective Reduction of Aldehydes, Ketones and Imines." International Journal of Molecular Sciences 23, no. 20 (2022): 12679. http://dx.doi.org/10.3390/ijms232012679.

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An operationally convenient Zn-catalyzed synthesis of alcohols by the reduction of aldehydes, ketones, and α,β-unsaturated aldehydes/ketones is reported. It is a rare example of using mild and sustainable HBpin as a reductant for catalytic reduction of carbonyl compounds in the absence of acid or base as hydrolysis reagent. The reaction is upscalable and proceeds in high selectivity without the formation of boronate ester by-products, and tolerates sensitive functionalities, such as iodo, bromo, chloro, fluoro, nitro, trifluoromethyl, aminomethyl, alkynyl, and amide. The Zn(OAc)2/HBpin combina

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47

Comas-Barceló, Júlia, Daniel Blanco-Ania, Sebastiaan A. M. W. van den Broek, Pieter J. Nieuwland, Joseph P. A. Harrity, and Floris P. J. T. Rutjes. "Cu-catalysed pyrazole synthesis in continuous flow." Catalysis Science & Technology 6, no. 13 (2016): 4718–23. http://dx.doi.org/10.1039/c5cy02247a.

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By using supported Cu(ii) catalysts for the regioselective synthesis of 1,4-disubstituted pyrazoles, we significantly reduced the Cu loading to 30 mol% and the alkyne required. Also, continuous flow allowed a dramatic reduction of reaction times going from 16 h to residence times of 5–15 min, being able to easily scale up this methodology.

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48

Khlebnikova, T. S., V. G. Isakova, A. V. Baranovskii, and F. A. Lakhvich. "Regioselective reduction of 2-perfluoroalkanoylcyclohexane-1,3-diones and their enamino derivatives." Russian Journal of General Chemistry 81, no. 4 (2011): 672–79. http://dx.doi.org/10.1134/s1070363211040098.

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49

Debenham, Sheryl D., and Eric J. Toone. "Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3·Et2O." Tetrahedron: Asymmetry 11, no. 2 (2000): 385–87. http://dx.doi.org/10.1016/s0957-4166(99)00584-4.

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Link, J. T., and Samuel J. Danishefsky. "Regioselective imide reduction : An issue in the total synthesis of staurosporine." Tetrahedron Letters 35, no. 49 (1994): 9135–38. http://dx.doi.org/10.1016/0040-4039(94)88446-3.

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