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Journal articles on the topic 'Hydrobenzoin'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Torres-Werlé, Maria, Adela Nano, Aline Maisse-François, and Stéphane Bellemin-Laponnaz. "Asymmetric benzoylation and Henry reaction using reusable polytopic bis(oxazoline) ligands and copper(ii)." New J. Chem. 38, no. 10 (2014): 4748–53. http://dx.doi.org/10.1039/c4nj00653d.

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Multitopic bis(oxazoline)-based chiral ligands are associated with copper to generate catalysts for the asymmetric benzoylation of meso-hydrobenzoin, the kinetic resolution of rac-hydrobenzoin and the asymmetric Henry reaction.

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2

Nemcsok, Tamás, Zsolt Rapi, Péter Bagi, Attila Oláh, György Keglevich, and Péter Bakó. "The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts." Catalysis Letters 150, no. 4 (2019): 930–38. http://dx.doi.org/10.1007/s10562-019-03013-0.

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Abstract New recyclable monoaza-15-crown ethers have been synthesized starting from (R,R)-(+)- and (S,S)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectiv

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3

Cho, Inhee, Labros Meimetis, Lee Belding, Michael J. Katz, Travis Dudding, and Robert Britton. "Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis." Beilstein Journal of Organic Chemistry 7 (September 22, 2011): 1315–22. http://dx.doi.org/10.3762/bjoc.7.154.

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A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.

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4

Bieging, Anna, Li-Xin Liao, and Dominic V. McGrath. "Hydrobenzoin-based rigid chiral polymer." Chirality 14, no. 2-3 (2002): 258–63. http://dx.doi.org/10.1002/chir.10070.

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5

Okano, Kazuya. "Synthesis and application of chiral hydrobenzoin." Tetrahedron 67, no. 14 (2011): 2483–512. http://dx.doi.org/10.1016/j.tet.2011.01.044.

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6

Maeda, Chihiro, and Tadashi Ema. "Chiral carbazole-based porphyrins showing absorption and circular dichroism in the near-infrared region." Journal of Porphyrins and Phthalocyanines 24, no. 01n03 (2020): 247–51. http://dx.doi.org/10.1142/s1088424619500937.

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Chiral carbazole-based porphyrins were synthesized for the first time via the incorporation of hydrobenzoin units at the thiophene moieties. They showed absorption and circular dichroism in the near-infrared (NIR) region. The NIR absorption was further red-shifted by solvent-induced aggregation.

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7

Shiau, Lie-Ding, Keng-Fu Liu, and Pin-Hao Huang. "Purification of hydrobenzoin enantiomers by stripping crystallization." Journal of the Taiwan Institute of Chemical Engineers 44, no. 5 (2013): 707–12. http://dx.doi.org/10.1016/j.jtice.2013.01.020.

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8

Gärtner, P., C. Schuster, and M. Knollmüller. "Polymer-Supported m-Hydrobenzoin-Derived Chiral Auxiliary." Synfacts 2007, no. 1 (2007): 0115. http://dx.doi.org/10.1055/s-2006-955692.

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9

Vedejs, E., O. Daugulis, and N. Tuttle. "Desymmetrization ofmeso-Hydrobenzoin Using Chiral, Nucleophilic Phosphine Catalysts." Journal of Organic Chemistry 69, no. 4 (2004): 1389–92. http://dx.doi.org/10.1021/jo030279c.

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10

Nicolosi, Giovanni, Angela Patti, Mario Piattelli, and Claudia Sanfilippo. "Desymmetrization of meso-hydrobenzoin via stereoselective enzymatic esterification." Tetrahedron: Asymmetry 5, no. 2 (1994): 283–88. http://dx.doi.org/10.1016/s0957-4166(00)86185-6.

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11

White, Rick C., and Terrell Rix. "Photolysis of meso- and d,l-hydrobenzoin carbonate." Journal of Organic Chemistry 52, no. 11 (1987): 2309–11. http://dx.doi.org/10.1021/jo00387a040.

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12

Okano, Kazuya. "ChemInform Abstract: Synthesis and Application of Chiral Hydrobenzoin." ChemInform 42, no. 35 (2011): no. http://dx.doi.org/10.1002/chin.201135223.

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13

Demir, Ayhan S., Haluk Hamamci, Peruze Ayhan, A. Nese Duygu, A. Cigdem İgdir, and Doga Capanoglu. "Fungi mediated conversion of benzil to benzoin and hydrobenzoin." Tetrahedron: Asymmetry 15, no. 16 (2004): 2579–82. http://dx.doi.org/10.1016/j.tetasy.2004.07.010.

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14

Zheltukhin, V. F., A. I. Dovbysh, D. N. Sadkova, et al. "Synthesis of stereoisomeric P—H-spirophosphoranes based on hydrobenzoin." Russian Chemical Bulletin 54, no. 8 (2005): 1935–38. http://dx.doi.org/10.1007/s11172-006-0060-2.

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15

Noe, Christian R., Max Knollmüller, Gerhard Steinbauer, and Horst Völlenkle. "Chirale Lactole, V. Synthese von (S)-Benzoin ausmeso-Hydrobenzoin." Chemische Berichte 118, no. 11 (1985): 4453–58. http://dx.doi.org/10.1002/cber.19851181116.

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16

Buisson, Didier, Sana El Baba, and Robert Azerad. "Yeast-catalyzed asymmetric reduction of benzil and benzoin to hydrobenzoin." Tetrahedron Letters 27, no. 37 (1986): 4453–54. http://dx.doi.org/10.1016/s0040-4039(00)84976-x.

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17

NICOLOSI, G., A. PATTI, M. PIATTELLI, and C. SANFILIPPO. "ChemInform Abstract: Desymmetrization of meso-Hydrobenzoin via Stereoselective Enzymatic Esterification." ChemInform 25, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199428067.

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18

Gong, Li, Chao Yue Zhang, Xiao Mu, et al. "Semiconductor nanosheets for electrocatalytic self-coupling of benzaldehyde to hydrobenzoin." Chemical Engineering Journal 479 (January 2024): 147612. http://dx.doi.org/10.1016/j.cej.2023.147612.

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19

Gong, Li, Chao Yue Zhang, Xiao Mu, et al. "Semiconductor nanosheets for electrocatalytic self-coupling of benzaldehyde to hydrobenzoin." Chemical Engineering Journal 479 (January 1, 2024): 147612. https://doi.org/10.1016/j.cej.2023.147612.

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The electrochemical reduction of biomass-derived feedstocks provides a sustainable platform for the synthesis of a wide range of chemical commodities and biofuels. Despite their interest, the optimization of reaction conditions, the screening of electrode materials, and the mechanistic understanding of these processes lag well behind other chemical routes. Here, we focus on the electrochemical self-coupling of benzaldehyde (BZH) to hydrobenzoin (HDB) using semiconductor electrocatalysts with nanosheet morphologies. By testing several semiconductor materials, a correlation is observed between t

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20

Li, Ji-Tai, Xiao-Ru Liu, and Xian-Feng Liu. "Oxidative cleavage of hydrobenzoin by ACC/silica gel under ultrasound irradiation." Ultrasonics Sonochemistry 16, no. 1 (2009): 4–6. http://dx.doi.org/10.1016/j.ultsonch.2008.06.004.

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21

Schuster, Christian, Joachim Broeker, Max Knollmueller та Peter Gaertner. "Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters". Tetrahedron: Asymmetry 16, № 15 (2005): 2631–47. http://dx.doi.org/10.1016/j.tetasy.2005.06.033.

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22

Cho, Inhee, Labros Meimetis, and Robert Britton. "Bidirectional Metalation of Hydrobenzoin: Direct Access to New Chiral Ligands and Auxiliaries." Organic Letters 11, no. 9 (2009): 1903–6. http://dx.doi.org/10.1021/ol900323u.

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23

Percino, María J., Víctor M. Chapela, and Roberto Ortega-Martínez. "Synthesis, characterization and evaluation of nonlinear optical properties of chiral hydrobenzoin monomers." Designed Monomers and Polymers 7, no. 5 (2004): 435–44. http://dx.doi.org/10.1163/1568555041872788.

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24

Schmid, Martin G., Birgit Härringer, Gerald Gübitz, and Klára Szabó. "Chiral Resolution ofRR,SS-Hydrobenzoin by Liquid Chromatography Using Borate-Cyclodextrin Complexation." Journal of High Resolution Chromatography 21, no. 7 (1998): 414–16. http://dx.doi.org/10.1002/(sici)1521-4168(19980701)21:7<414::aid-jhrc414>3.0.co;2-n.

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25

Campestrini, Sandro, Fulvio Di Furia, and Fabiola Novello. "Oxidation of meso- and d,l-hydrobenzoin by peroxomolybdenum complexes: A mechanistic investigation." Journal of Molecular Catalysis 78, no. 2 (1993): 159–68. http://dx.doi.org/10.1016/0304-5102(93)85035-r.

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26

Arai, Takayoshi, and Ken Sakagami. "Asymmetric Benzoylation of meso-Hydrobenzoin Using a Reusable Tripodal Imidazoline-Pyridine-Cu Catalyst." European Journal of Organic Chemistry 2012, no. 6 (2012): 1097–100. http://dx.doi.org/10.1002/ejoc.201101722.

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27

Pennington, William T., Sumita Chakraborty, Iain C. Paul, and D. Y. Curtin. "Crystal structures of D-(+)- and meso-hydrobenzoin. Absolute direction of the dipole moment of D- and L-hydrobenzoin in the crystal and correlation with crystal morphology, pyroelectric effect, and absolute configuration." Journal of the American Chemical Society 110, no. 19 (1988): 6498–504. http://dx.doi.org/10.1021/ja00227a034.

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28

Wang, Zhi-Min, and K. Barry Sharpless. "A Solid-to-Solid Asymmetric Dihydroxylation Procedure for Kilogram-Scale Preparation of Enantiopure Hydrobenzoin." Journal of Organic Chemistry 59, no. 26 (1994): 8302–3. http://dx.doi.org/10.1021/jo00105a065.

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29

Zhang, Meiyu, Kongming Li, Chunlian Hu, et al. "Co nanoparticles modified phase junction CdS for photoredox synthesis of hydrobenzoin and hydrogen evolution." Chinese Journal of Catalysis 47 (April 2023): 254–64. http://dx.doi.org/10.1016/s1872-2067(23)64393-1.

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30

Ozenil, Marius, Jonas Aronow, Daniela Piljak, et al. "Synthesis, Biological, and Computational Evaluation of Antagonistic, Chiral Hydrobenzoin Esters of Arecaidine Targeting mAChR M1." Pharmaceuticals 13, no. 12 (2020): 437. http://dx.doi.org/10.3390/ph13120437.

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Muscarinic acetylcholine receptors (mAChRs) are a pivotal constituent of the central and peripheral nervous system. Yet, therapeutic and diagnostic applications thereof are hampered by the lack of subtype selective ligands. Within this work, we synthesized and chemically characterized three different stereoisomers of hydrobenzoin esters of arecaidine by NMR, HR-MS, chiral chromatography, and HPLC-logP. All compounds are structurally eligible for carbon-11 labeling and show appropriate stability in Dulbecco’s phosphate-buffered saline (DPBS) and F12 cell culture medium. A competitive radioligan

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31

Kim, Kwan Soo, Jong Park, and Pingyu Ding. "Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin." Tetrahedron Letters 39, no. 36 (1998): 6471–74. http://dx.doi.org/10.1016/s0040-4039(98)01377-x.

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32

Fujioka, Hiromichi, Hidetoshi Kitagawa, Naoki Matsunaga, Yasushi Nagatomi, and Yasuyuki Kita. "Remote asymmetric induction for chiral 1,4-diols using a chiral acetal derived from chiral hydrobenzoin." Tetrahedron Letters 37, no. 13 (1996): 2245–48. http://dx.doi.org/10.1016/0040-4039(96)00266-3.

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33

Arai, Takayoshi, and Ken Sakagami. "ChemInform Abstract: Asymmetric Benzoylation of meso-Hydrobenzoin Using a Reusable Tripodal Imidazoline-Pyridine-Cu Catalyst." ChemInform 43, no. 28 (2012): no. http://dx.doi.org/10.1002/chin.201228091.

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34

Mash, Eugene A., and Daniel S. Torok. "Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation of .alpha.,.beta.-unsaturated ketals derived from (S,S)-(-)-hydrobenzoin." Journal of Organic Chemistry 54, no. 1 (1989): 250–53. http://dx.doi.org/10.1021/jo00262a054.

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35

Du, Yu, Dandan Feng, Jingwei Wan, and Xuebing Ma. "The enhanced asymmetric hydrogenation of unsymmetrical benzils to hydrobenzoin catalyzed by organosoluble zirconium phosphonate-immobilized ruthenium catalyst." Applied Catalysis A: General 479 (June 2014): 49–58. http://dx.doi.org/10.1016/j.apcata.2014.03.039.

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36

KIM, K. S., J. I. PARK, and P. DING. "ChemInform Abstract: Synthesis of Enantiopure Cyclopentitols and Aminocyclopentitols Mediated by Oxyselenenylation of Cyclopentene with (R,R)-Hydrobenzoin." ChemInform 29, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199848232.

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37

FUJIOKA, H., H. KITAGAWA, N. MATSUNAGA, Y. NAGATOMI, and Y. KITA. "ChemInform Abstract: Remote Asymmetric Induction for Chiral 1,4-Diols Using a Chiral Acetal Derived from Chiral Hydrobenzoin." ChemInform 27, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199628038.

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38

Gong, Li, Shiling Zhao, Jing Yu, et al. "Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin." Energy Advances 3, no. 9 (2024): 2287–94. https://doi.org/10.1039/D4YA00334A.

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The electroreduction of biomass-derived benzaldehyde (BZH) provides a potentially cost-effective route to produce benzyl alcohol (BA). This reaction competes with the electrochemical self-coupling of BZH to hydrobenzoin (HDB), which holds significance as a biofuel. Herein, we demonstrate the selectivity towards one or the other product strongly depends on the surface chemistry of the catalyst, specifically on its ability to adsorb hydrogen, as showcased with Cu<sub>2</sub>S electrocatalysts. We particularly analyze the effect of surface ligands, oleylamine (OAm), on the selective conversion of

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39

Klunder, Kevin J., Ashley C. Cass, Scott L. Anderson та Shelley D. Minteer. "Phthalocyanines as a π–π Adsorption Strategy to Immobilize Catalyst on Carbon for Electrochemical Synthesis". Synlett 30, № 10 (2019): 1187–93. http://dx.doi.org/10.1055/s-0037-1611792.

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In most electrochemical syntheses, reactions are happening at or near the electrode surface. For catalyzed reactions, ideally, the electrode surface would solely contain the catalyst, which then simplifies purification and lowers the amount of catalyst needed. Here, a new strategy involving phthalocyanines (Pc) to immobilize catalysts onto carbon electrode surfaces is presented. The large π structure of the Pc enables adsorption to the sp2-structure of graphitic carbon. TEMPO-modified Pc were chosen as a proof of concept to test the new immobilization strategy. It was found that the TEMPO-Pc d

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40

Silva, Ana Rosa, Liliana Carneiro, Ana P. Carvalho, and João Pires. "Asymmetric benzoylation of hydrobenzoin by copper(ii) bis(oxazoline) anchored onto ordered mesoporous silicas and their carbon replicas." Catalysis Science & Technology 3, no. 9 (2013): 2415. http://dx.doi.org/10.1039/c3cy00232b.

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41

Shabbir, S. H., C. J. Regan, and E. V. Anslyn. "A general protocol for creating high-throughput screening assays for reaction yield and enantiomeric excess applied to hydrobenzoin." Proceedings of the National Academy of Sciences 106, no. 26 (2009): 10487–92. http://dx.doi.org/10.1073/pnas.0809530106.

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42

Gök, Yaşar, Halil Zeki Gök, Mustafa Kemal Yılmaz, Murat Farsak, and İlker Ümit Karayiğit. "Novel peripherally and non-peripherally hydrobenzoin substituted optically active phthalocyanines: Synthesis, characterization, aggregation, electrochemical properties and catalytic applications." Polyhedron 153 (October 2018): 128–38. http://dx.doi.org/10.1016/j.poly.2018.06.053.

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43

Shi, Hui, Chuan Du, Xinhang Zhang, et al. "Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline." Journal of Organic Chemistry 83, no. 3 (2018): 1312–19. http://dx.doi.org/10.1021/acs.joc.7b02587.

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44

Wang, Yunwei, Pengju Ren, Xianmo Gu, et al. "Probing the mechanism of benzaldehyde reduction to chiral hydrobenzoin on the CNT surface under near-UV light irradiation." Green Chemistry 18, no. 6 (2016): 1482–87. http://dx.doi.org/10.1039/c5gc02168e.

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45

Yu, Guangyan, Lizhen Guo, Feiyun Xie, Bixia Yao, Qingle Zeng та Wen Weng. "Enantioseparation of Hydrobenzoin and Structurally Related Compounds on β-Cyclodextrin and Hydroxypropyl-β-cyclodextrin Bonded Chiral Stationary Phases". Chromatographia 73, № 11-12 (2011): 1049–55. http://dx.doi.org/10.1007/s10337-011-1995-5.

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46

Lin, Ching-Erh, Sheng-Li Lin, I.-Ju Fang, Wei-Ssu Liao та Chia-Chong Chen. "Enantioseparations of hydrobenzoin and structurally related compounds in capillary zone electrophoresis using heptakis(2,3-dihydroxy-6-O-sulfo)-β-cyclodextrin as chiral selector and enantiomer migration reversal of hydrobenzoin with a dual cyclodextrin system in the presence of borate complexation". ELECTROPHORESIS 25, № 16 (2004): 2786–94. http://dx.doi.org/10.1002/elps.200405968.

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47

Lu, Xinnan, Roxanne Clément, Yong Lu, Belén Albela, R. Tom Baker, and Laurent Bonneviot. "Selective C–C Bond Cleavage in Diols and Lignin Models: High-Throughput Screening of Metal Oxide-Anchored Vanadium in Mesoporous Silica." Catalysts 11, no. 8 (2021): 901. http://dx.doi.org/10.3390/catal11080901.

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The development of selective and robust heterogeneous oxidation catalysts is an enabling technology for conversion of biomass-derived platform chemicals. Vanadium active sites were incorporated into the structure of mesoporous silica via an ultra-fast, one-pot synthesis method based on microwave-assisted heating. In addition, Al/Ti/Zr/Ce anchoring ions were introduced in order to minimize vanadium leaching and better control its dispersion. The supported V-(Al/Ti/Zr/Ce)-MCM-41 composite materials were assessed as catalysts for aerobic C–C bond cleavage of simple models for lignin (1,2-diphenyl

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48

Gaertner, P., C. Schuster, and M. Knollmueller. "Chiral Linker 1. A Novel Chiral Auxiliary Derived from m-Hydrobenzoin as Enantiomerically Pure Linker for Solid Phase Organic Chemistry." Letters in Organic Chemistry 1, no. 3 (2004): 249–53. http://dx.doi.org/10.2174/1570178043400901.

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49

Kim, Kwan Soo, Yong Joo Lee, Jin Hwan Kim, and Da Kyung Sung. "Synthesis of (+)-polyoxamic acid and D-sorbitol from simple achiral allylic halides employing (S,S)-hydrobenzoin as a chiral source." Chemical Communications, no. 10 (April 18, 2002): 1116–17. http://dx.doi.org/10.1039/b202823a.

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50

Lin, Ching-Erh, Sheng-Li Lin, Wei-Ssu Liao, and Yu-Chih Liu. "Enantioseparation of benzoins and enantiomer migration reversal of hydrobenzoin in capillary zone electrophoresis with dual cyclodextrin systems and borate complexation." Journal of Chromatography A 1032, no. 1-2 (2004): 227–35. http://dx.doi.org/10.1016/j.chroma.2004.01.011.

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