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Journal articles on the topic 'Aldolic reaction'

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Published: 4 June 2021
Last updated: 7 February 2022

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1

Medina-Navarro, R., E. Mercado-Pichardo, O. Herńndez-Pérez, and J. J. Hicks. "Identification of acrolein from the ozone oxidation of unsaturated fatty acids." Human & Experimental Toxicology 18, no. 11 (1999): 677–82. http://dx.doi.org/10.1191/096032799678839527.

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By-products of lipoperoxidation reactions may be associated with the genesis or the progression of several diseases as arteriosclerosis, diabetes and cancer, among many others. Acrolein, at first a widely distributed environmental pollutant, is currently known as a compound capable of being generated as a result of metabolic reactions within biological systems, highly toxic and the most electrophilic of the a, b-unsaturated aldehydes formed during lipoperoxidation. In the present study: 1 The separation of acrolein and malondialdehyde was achieved at alkaline pH with the use of high voltage ca
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2

Cruz, Alejandro, Itzia I. Padilla-Martínez, and Maria E. Bautista-Ramirez. "Ephedrines as Chiral Auxiliaries in Enantioselective Alkylation Reactions of Acyl Ephedrine Amides and Esters: A Review." Current Organic Synthesis 15, no. 1 (2018): 38–83. http://dx.doi.org/10.2174/1570179414666170830125915.

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Background: In modern chemistry, the asymmetric synthesis for the preparation of high purity chiral compounds to be used as pharmaceuticals or additives in foods have been of capital importance. Chiral auxiliary reagents are used to control the stereochemistry of the reaction in the generation of new chiral compounds, in this context, Ephedra compounds (ephedrines and pseudoephedrines) and some of their derivatives have been broadly used as chiral ligands in catalysis or chiral inductors in asymmetric synthesis. Objective: This review focuses on recent progress in the use of ephedra compounds
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3

Hernández-Rodríguez, Marcos, Claudia Gabriela Avila-Ortiz, Jorge M. del Campo, Delia Hernández-Romero, María J. Rosales-Hoz, and Eusebio Juaristi. "Synthesis of Novel Chiral (Thio)ureas and Their Application as Organocatalysts and Ligands in Asymmetric Synthesis." Australian Journal of Chemistry 61, no. 5 (2008): 364. http://dx.doi.org/10.1071/ch08116.

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The synthesis of novel chiral (thio)ureas 1–10 and 14–26 is described. These (thio)ureas incorporate chiral auxiliaries derived from (R)- or (S)-α-phenylethylamine, (R)-phenylglycine, or (1R,2S)-ephedrine. The phenylethyl group in compounds 1–10 and 21–24 adopts a particular orientation in the molecular structure as a consequence of 1,3-allylic strain with the (thio)carbonyl group. Ureas 1–10 were tested as Lewis basic organocatalysts in epoxide ring opening and in aldolic condensation, and it was found that the tetrasubstituted urea (R,R)-2 afforded the best results in terms of reaction yield
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4

Dammene Debbih, Ouafa, Assia Sid, Rafika Bouchene, Sofiane Bouacida, Wissam Mazouz, and Noureddine Gherraf. "Two hydrazones derived from 1-aryl-3-(p-substituted phenyl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface analysis andin vitrobiological properties." Acta Crystallographica Section C Structural Chemistry 74, no. 6 (2018): 703–14. http://dx.doi.org/10.1107/s2053229618006812.

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Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen–Schmidt reaction conditions and then treated with 2,4-dinitrophenylhydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-dinitrophenylhydrazone structures, namely (Z)-1-(2,4-dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine, C22H18N4O4, (H1), and (Z)-1-[(E)-3-(4-chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine, C25H17ClN4O4, (H2), were isolated by recrystallization and characterized by FT–IR, UV–Vis,
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5

Schreyer, Lucas, Philip S. J. Kaib, Vijay N. Wakchaure, et al. "Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates." Science 362, no. 6411 (2018): 216–19. http://dx.doi.org/10.1126/science.aau0817.

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Reactions that form a product with the same reactive functionality as that of one of the starting compounds frequently end in oligomerization. As a salient example, selective aldol coupling of the smallest, though arguably most useful, enolizable aldehyde, acetaldehyde, with just one partner substrate has proven to be extremely challenging. Here, we report a highly enantioselective Mukaiyama aldol reaction with the simple triethylsilyl (TES) andtert-butyldimethylsilyl (TBS) enolates of acetaldehyde and various aliphatic and aromatic acceptor aldehydes. The reaction is catalyzed by recently dev
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6

Hayashi, Yujiro, and Itaru Sato. "Mukaiyama Aldol Reaction ^|^mdash; 40th Anniversary Symposium." Journal of Synthetic Organic Chemistry, Japan 72, no. 3 (2014): 309–13. http://dx.doi.org/10.5059/yukigoseikyokaishi.72.309.

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7

Müller, Tobias, Kristina Djanashvili, Joop A. Peters, Isabel W. C. E. Arends, and Ulf Hanefeld. "Tetrahedral boronates as basic catalysts in the aldol reaction." Zeitschrift für Naturforschung B 70, no. 8 (2015): 587–95. http://dx.doi.org/10.1515/znb-2015-0029.

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Abstractβ-Hydroxyketones are versatile building blocks in organic synthesis, which can be conveniently synthesized from ketones and aldehydes by aldol reactions. Unfortunately, these reactions often suffer from dehydration of the initially formed β-hydroxyketones. Previously, tetrahedral 3,5-difluorophenylborate was shown to be an efficient and selective catalyst for this reaction. The present investigation concerns the catalytic performance of phenyl borates with different substitution patterns in the aldol reaction. It appears that the dehydration reaction can be suppressed by selecting subs
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8

Huang, Wen-Ping, Jia-Rong Chen, Xin-Yong Li, Yi-Ju Cao, and Wen-Jing Xiao. "Asymmetric organocatalytic direct aldol reactions of cyclohexanone with aldehydes in brine." Canadian Journal of Chemistry 85, no. 3 (2007): 208–13. http://dx.doi.org/10.1139/v07-012.

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Organocatalytic asymmetric direct aldol reactions in brine with high diastereo- and enantioselectivities, using a readily available bifunctional amide catalyst, were developed.Key words: aldol reaction, organocatalyst, asymmetric catalysis, water.
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9

Inegbenebor, Adedayo I., Raphael C. Mordi, and Oluwakayode M. Ogunwole. "Zeolite Catalyzed Aldol Condensation Reactions." International Journal of Applied Sciences and Biotechnology 3, no. 1 (2015): 1–8. http://dx.doi.org/10.3126/ijasbt.v3i1.12291.

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The review is based on the description of zeolite structure, uses, synthesis, and catalytic aldol reaction in aldol condensation. An internal aldolcondensation reaction has been achieved over ZSM-5 zeolite with high silica-alumina ratio at 350oC. It therefore follows that zeolite canfunction as a catalyst in aldol type condensation reactions and that weak acid sites as well as a small number of active sites favor the aldolcondensation reaction of carbonyl compounds. However, the mixed condensation product was found to be favored at temperatures above 300oCand the self-condensation of ethanal t
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10

Rougeot, Céline, Henry Situ, Blessing Huynh Cao, Vaso Vlachos, and Jason E. Hein. "Automated reaction progress monitoring of heterogeneous reactions: crystallization-induced stereoselectivity in amine-catalyzed aldol reactions." Reaction Chemistry & Engineering 2, no. 2 (2017): 226–31. http://dx.doi.org/10.1039/c6re00211k.

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11

Singh, Girija S. "Greener Approaches to Selected Asymmetric Addition Reactions Relevant to Drug Development." Current Organic Chemistry 25, no. 13 (2021): 1497–522. http://dx.doi.org/10.2174/1385272825666210519100457.

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Asymmetric organic synthesis is of paramount importance in the development of drugs. Asymmetric addition reactions such as aldol reaction, Michael addition, and Mannich addition reactions are important carbon-carbon bond-forming reactions and have been employed in the synthesis of a broad range of biologically important molecules. Many of these reactions have been developed under solvent-free conditions or in greener solvents like water. Several reactions have been developed at room temperature or by using a non-conventional energy source such as microwave irradiation. Several greener catalyst
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12

Sugita, Kazuyuki, Motoi Kuwabara, Ami Matsuo, Shogo Kamo, and Akinobu Matsuzawa. "Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone." Synthesis 53, no. 12 (2021): 2092–102. http://dx.doi.org/10.1055/s-0040-1706684.

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AbstractIn this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing meta­thesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.
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13

Dreier, Anna-Lena, Andrej V. Matsnev, Joseph S. Thrasher та Günter Haufe. "Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes". Beilstein Journal of Organic Chemistry 14 (8 лютого 2018): 373–80. http://dx.doi.org/10.3762/bjoc.14.25.

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Aldol reactions belong to the most frequently used C–C bond forming transformations utilized particularly for the construction of complex structures. The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ6-sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with high diastereoselectivity. In case of benzaldehydes with electron-withdrawing substituents in the para-position, syn-α-SF5-β-hydroxyalkanoic acid es
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14

Ashokkumar, Veeramanoharan, Chinnadurai Chithiraikumar, and Ayyanar Siva. "Binaphthyl-based chiral bifunctional organocatalysts for water mediated asymmetric List–Lerner–Barbas aldol reactions." Organic & Biomolecular Chemistry 14, no. 38 (2016): 9021–32. http://dx.doi.org/10.1039/c6ob01558a.

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Binaphthyl-based organocatalysts were synthesized and successfully applied to the asymmetric List–Lerner–Barbas aldol reaction in water medium. These organocatalysts were found to be effective catalysts for the reactions of ketones with different aldehydes to give aldol products with higher yield and ee's.
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15

Saikia, Hemaprobha, and Sanjay Basumatary. "MgRuAl-layered Double Hydroxides (LDH): An Efficient Multifunctional Catalyst for Aldol Condensation and Transfer Hydrogenation Reactions." Current Catalysis 8, no. 1 (2019): 62–69. http://dx.doi.org/10.2174/2211550108666190418125857.

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Background: Layered double hydroxides (LDH) are drawing much attention as solid catalysts in recent years and have applications in various organic transformations as they possess a variety of basic sites which could be obtained by exchange of metal ions or by intercalation of suitable anions into their interlayer space. Ru based complexes have widespread catalytic applications in many organic reactions. Herein, novel ruthenium containing ternary LDH has been synthesized and used as a multifunctional catalyst for Aldol condensation and transfer hydrogenation reactions. Methods: Ternary LDH mult
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16

Lee, Hyo-Jun, Natarajan Arumugam, Abdulrahman Almansour, Raju Kumar, and Keiji Maruoka. "Design of New Amino Tf-Amide Organocatalysts: Environmentally Benign Approach to Asymmetric Aldol Synthesis." Synlett 30, no. 04 (2018): 401–4. http://dx.doi.org/10.1055/s-0037-1610408.

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A new type of optically pure primary amino aromatic Tf-amide organocatalyst can be easily prepared from 8-amino-1-tetralone, and its chemical behavior was investigated in the context of asymmetric aldol and Mannich reactions. Most notably, the asymmetric aldol reaction proceeded smoothly in brine.
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17

Cordes, Martin, and Markus Kalesse. "Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis." Molecules 24, no. 17 (2019): 3040. http://dx.doi.org/10.3390/molecules24173040.

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It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction is the most important transformation to generate this structural element as it not only creates new C–C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies of aldol and aldol-type reactions have been put forward. In this regard, the vinyl
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18

Kagawa, Natsuko, Masahiro Toyota, and Masataka Ihara. "Yb(OTf)3 - TMSCl, a Novel Catalytic System in Cross-Aldol Reactions." Australian Journal of Chemistry 57, no. 7 (2004): 655. http://dx.doi.org/10.1071/ch04006.

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A combination of Yb(OTf)3 and TMSCl influenced the outcome of cross-aldol reactions of cycloalkanones and benzaldehyde. Interestingly, reaction of cycloheptanone and cyclooctanone with aldehydes under the Yb(OTf)3–TMSCl reagent system provides 3-(2-oxocycloalkyl)-3-phenylpropanals in conjunction with the corresponding aldol products.
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19

Vuk, Dragana, Irena Škorić, Valentina Milašinović, Krešimir Molčanov, and Željko Marinić. "A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes." Beilstein Journal of Organic Chemistry 16 (May 22, 2020): 1092–99. http://dx.doi.org/10.3762/bjoc.16.96.

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In order to prepare novel polycyclic derivatives of bicyclo[3.2.1]octadiene systems fused with a thiophene ring, photochemical cyclization and aldol condensation reactions were carried out. The starting substrates were easily obtained by a Vilsmeier–Haack reaction of bicyclo[3.2.1]octadiene thiophene derivatives with dimethylformamide. From the obtained carbaldehydes, novel methyl, methoxy, and cyano-substituted styryl thienobenzobicyclo[3.2.1]octadiene derivatives were synthesized through Wittig reactions and subjected to photochemical cyclization, in terms of obtaining the new annulated stru
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20

Lazny, Ryszard, Aneta Nodzewska, Katarzyna Sidorowicz, and Przemyslaw Kalicki. "Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers." Beilstein Journal of Organic Chemistry 8 (November 2, 2012): 1877–83. http://dx.doi.org/10.3762/bjoc.8.216.

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The relative configurations oftert-butyldimethylsilyl (TBDMS) ethers of all four diastereomers of the aldols of tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one), as well as of granatanone (9-methyl-9-azabicyclo[3.3.1]nonan-3-one), were determined from NMR data, and from the observed interconversion of the diastereomers (exo,antitoendo,synandexo,syntoendo,anti). Theexoforms invert toendoisomers in the presence of silica gel. The relative configuration of a new isomer of tropinone aldol accessible synthetically through the direct solventless reaction of tropinone and benzaldehyde in the prese
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21

Kaewmee, Benyapa, Vatcharin Rukachaisirikul, and Juthanat Kaeobamrung. "Synthesis of quinolines via copper-catalyzed domino reactions of enaminones." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7387–95. http://dx.doi.org/10.1039/c7ob01867c.

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22

Eaton, Richard W. "trans-o-Hydroxybenzylidenepyruvate Hydratase-Aldolase as a Biocatalyst." Applied and Environmental Microbiology 66, no. 6 (2000): 2668–72. http://dx.doi.org/10.1128/aem.66.6.2668-2672.2000.

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ABSTRACT The hydratase-aldolase-catalyzed conversion oftrans-o-hydroxybenzylidenepyruvate to salicylaldehyde and pyruvate is an intermediate reaction in the conversion of naphthalene to salicylate by bacteria. Here, a variety of aromatic aldehydes and some nonaromatic aldehydes together with pyruvate have been shown to be substrates for aldol condensations catalyzed by this enzyme in extracts of the recombinant strain Escherichia coli JM109(pRE701). Some of the products of these reactions were also compared as substrates in the opposite (hydration-aldol cleavage) reaction.
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23

Schneider, Christoph, Markus Hansch, and Timo Weide. "The Zirconium Alkoxide-Catalyzed Aldol-Tishchenko Reaction of Ketone Aldols." Chemistry - A European Journal 11, no. 10 (2005): 3010–21. http://dx.doi.org/10.1002/chem.200400951.

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24

Sodeoka, Mikiko, and Yoshitaka Hamashima. "Synthesis of optically active heterocyclic compounds using Pd-catalyzed asymmetric reactions as a key step." Pure and Applied Chemistry 80, no. 4 (2008): 763–76. http://dx.doi.org/10.1351/pac200880040763.

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Highly enantioselective Pd(II)-catalyzed Michael addition, Mannich-type reaction, aldol reaction, fluorination, conjugate addition of amine, and conjugate reduction have been developed. Asymmetric synthesis of biologically interesting heterocyclic compounds, calycotomine, BMS-204352, torcetrapib, and warfarin, was achieved by using these Pd-catalyzed asymmetric reactions as a key step.
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25

Lazny, Ryszard, Artur Ratkiewicz, Krzysztof Brzezinski, Aneta Nodzewska, and Katarzyna Sidorowicz. "An Investigation of the Enolization and Isomeric Products Distribution in the Water Promoted Aldol Reaction of Tropinone and Granatanone." Journal of Chemistry 2016 (2016): 1–15. http://dx.doi.org/10.1155/2016/4674901.

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The exo,anti/exo,syn-diastereoselectivity of water promoted direct aldol reactions of tropinone and granatanone (pseudopelletierine) is strongly dependent on the amount of water added and aromatic aldehyde used. DFT methods were applied to calculate the free energies of tropinone and granatanone enols, transition states, and isomeric aldol products. A theoretical model was verified by comparison of results from several DFT methods and functionals with experiments. The 6-31g(d)/CPCM method proved most suited to the problem, although all methods tested predicted similar trends. Explicit inclusio
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26

Zhao, Cheng Yan, Ai Ping Fu, Hong Liang Li, Ping Wang, Yong Xu, and Yun Bo Duan. "Theoretical Study of Stereoselectivity for Syn-Selective Cross-Aldol Reactions of Aldehydes Catalyzed by Chiral Diamine Organocatalysts." Advanced Materials Research 798-799 (September 2013): 59–62. http://dx.doi.org/10.4028/www.scientific.net/amr.798-799.59.

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Quantum mechanical calculations have been performed to study the stereoselectivities in the direct cross-aldol reactions of aldehydes catalyzed by simple chiral diamines. The detailed computational studies on the stereochemistry-controlling step of the subject reactions have been presented by DFT calculations at the B3LYP/6-31G* level. The poor agreement between the calculated and the observed diastereomeric ratio and enantiomeric excess values is obtained for all diamines catalysts. Further M06-2X calculations can provide a reasonable explanation for the observed syn-selectivities of the asym
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27

Wang, Heng, Na Li, Zijia Yan, Jie Zhang, and Xinhua Wan. "Synthesis and properties of novel helical 3-vinylpyridine polymers containing proline moieties for asymmetric aldol reaction." RSC Advances 5, no. 65 (2015): 52410–19. http://dx.doi.org/10.1039/c5ra07207g.

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Novel helical vinyl polymers bearing l/d-proline amide moieties were prepared to catalyze asymmetric aldol reactions, which afforded faster reaction rate but slightly poorer enantio-selectivity than the low molar mass counterparts.
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28

Leal, Glauco F., Silvia F. Moya, Debora M. Meira, et al. "Promotion effects of Pd on tungsten carbide catalysts: physiochemical properties and cellulose conversion performance." RSC Advances 6, no. 90 (2016): 87756–66. http://dx.doi.org/10.1039/c6ra15819f.

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A multi-functional catalyst, which is able to perform both retro-aldol reactions followed by hydrogenation, is required to convert cellulose into value-added chemicals such as ethylene glycol (EG) in a one-pot reaction.
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29

Li, Guangxun, Zhuo Tang, Hongxin Liu, Ying-wei Wang, and Shiqi Zhang. "Bioinspired Catalysis: Self-Assembly of a Protein and DNA as a Catalyst for the Aldol Reaction in Aqueous Media." Synlett 29, no. 05 (2017): 560–65. http://dx.doi.org/10.1055/s-0036-1591854.

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An interesting bioinspired catalyst formed from readily available DNA and a protein through electrostatic interaction in situ proved to be efficient in catalyzing aldol reactions under mild conditions in water. By using a self-assembling catalytic system formed from protamine and DNA, aldol adducts were obtained with high yields and moderate enantioselectivities. Preliminary experiments demonstrated that the chirality of the DNA could be effectively transferred to the reaction product through the bound molecules or proteins.
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30

Rossi, Sergio, Tiziana Benincori, Laura Maria Raimondi, and Maurizio Benaglia. "3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions." Synlett 31, no. 06 (2020): 535–46. http://dx.doi.org/10.1055/s-0039-1690777.

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This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are d
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31

Nguyen, Kim, and David W. Lupton. "N-Heterocyclic Carbene-Catalysed Mukaiyama–Michael Reaction and Mukaiyama Aldol/Mukaiyama–Michael Three-Component Coupling Reaction." Australian Journal of Chemistry 70, no. 4 (2017): 436. http://dx.doi.org/10.1071/ch16566.

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An N-heterocyclic carbene-catalysed Mukaiyama–Michael addition between several trimethylsilyl (TMS) enol ethers and chalcone derivatives has been discovered. In addition, a related reaction cascade involving dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The later reaction can also be achieved as a three-component coupling reaction. The enantioselective variant of these reactions has been examined with homochiral catalysts. Though these catalysts were active, they fail to achieve enantioinduction.
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32

Lubineau, Andre. "Water-promoted organic reactions: aldol reaction under neutral conditions." Journal of Organic Chemistry 51, no. 11 (1986): 2142–44. http://dx.doi.org/10.1021/jo00361a045.

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33

Dodda, Rajasekhar, Sampak Samanta, Matthew Su, and John Cong-Gui Zhao. "Synthesis of 1,2-Diamine Bifunctional Catalysts for the Direct Aldol Reaction Through Probing the Remote Amide Hydrogen." Current Organocatalysis 6, no. 2 (2019): 171–76. http://dx.doi.org/10.2174/2213337206666190301155247.

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Background: While proline can catalyze the asymmetric direct aldol reactions, its catalytic activity and catalyst turnover are both low. To improve the catalytic efficiency, many prolinebased organocatalysts have been developed. In this regard, prolinamide-based bifunctional catalysts have been demonstrated by us and others to be highly efficient catalysts for the direct aldol reactions. Results: Using the β-acetamido- and β-tosylamidoprolinamide catalysts, the highly enantio- and diastereoselective direct aldol reactions between enolizable ketones and aldehydes were achieved (up to >99% ee
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34

Wan, Peter, and S. Muralidharan. "Photochemical retro-aldol type reactions of nitrobenzyl derivatives. Mechanistic variations in the elimination of nitrobenzyl carbanions from nitrobenzyl derivatives on photolysis." Canadian Journal of Chemistry 64, no. 9 (1986): 1949–51. http://dx.doi.org/10.1139/v86-321.

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The photochemical retro-aldol type reactions of several nitrobenzyl derivatives are reported. The reactions are observed only in aqueous solution with quantum efficiencies being pH dependent for several derivatives, consistent with the existence of several mechanistic pathways for reaction. The primary photochemical event is believed to involve the generation of a nitrobenzyl carbanion, which acts as a photolabile leaving group in these reactions, and the generation of an oxocarbocation (or oxocarbocation-derived) fragment.
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35

Sánchez-Antonio, Omar, Kevin A. Romero-Sedglach, Erika C. Vázquez-Orta, and Eusebio Juaristi. "New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction." Molecules 25, no. 19 (2020): 4532. http://dx.doi.org/10.3390/molecules25194532.

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Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction. These materials were fully characterized by FT-IR, MS, XRD, and SEM microscopy, gathering relevant information regarding composition, morphology, and organocatalyst distribution in the doped silica. Careful optimization of the reaction conditions required for their application as catalysts in asymmetric aldol reactions between ketones a
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36

Hagiwara, Hisahiro, Masakazu Fukushima, Kimihiko Kinugawa, Takuya Matsui, Takashi Hoshi, and Toshio Suzuki. "Total Synthesis of the Bicyclic Marine Sesquiterpenoid Drechslerine B." Natural Product Communications 6, no. 3 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600302.

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The total synthesis of the recently isolated bicyclic sesquiterpenoid drechslerine B (2), isolated from the algicolous fungus Drechslera dematioidearare in the marine red alga Liagora viscida, has been achieved, starting from ( S)-carvone (8), via an intramolecular aldol reaction and palladium-catalyzed carbon monoxide insertion as key reactions.
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37

Bertrand, Myra Beaudoin, and John P. Wolfe. "Tandem Wittig Rearrangement/Aldol Reactions for the Synthesis of Glycolate Aldols." Organic Letters 8, no. 20 (2006): 4661–63. http://dx.doi.org/10.1021/ol062016l.

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38

Schneider, Christoph, Markus Hansch, and Pankajakshan Sreekumar. "Zirconium–BINOLate-catalyzed, enantioselective aldol-Tishchenko reactions of aromatic ketone aldols." Tetrahedron: Asymmetry 17, no. 19 (2006): 2738–42. http://dx.doi.org/10.1016/j.tetasy.2006.10.019.

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39

Xu, Jiafang, Jichao Liang, Sheng Huang, et al. "On the Exceptionally High Loading of L-Proline on Multi-Wall Carbon Nanotubes." Catalysts 10, no. 11 (2020): 1246. http://dx.doi.org/10.3390/catal10111246.

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L-proline is directly loaded on the multi-wall carbon nanotubes (MWCNTs) with exceptionally high loading content of 67 wt.%. The obtained L-proline/MWCNTs catalyst is on par with the catalytic activity of free L-proline, even after 7 rounds of recycling and reusing. The excellent activity of L-proline/MWCNTs in typical Aldol reaction, Mannich reaction, Michael reaction, α-oxyamination reaction, and Knoevenagel condensation shows a broad applicability of the composite catalyst in different reactions and solvent systems. We believe that the unusual loading mode may open a window for designing he
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40

Hudlický, Miloš. "The Wichterle Reaction." Collection of Czechoslovak Chemical Communications 58, no. 10 (1993): 2229–44. http://dx.doi.org/10.1135/cccc19932229.

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The Wichterle reaction is a conversion of vinylic chlorides to ketones by sulfuric acid. Most of the applications are transformations of γ-chlorocrotyl (3-chloro-2-butenyl) derivatives to 3-oxobutyl derivatives. The ketones thus formed may undergo subsequent reactions in compounds containing reactive centers. Thus intramolecular aldol-type condensations occur in compounds containing carbonyl groups, and Friedel-Crafts-type cyclizations in compounds containing aromatic rings. The reaction can be used as an alternative to Robinson's annelation.
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41

Jing, Tao, Jing Zhi Tian, and De Zhi Sun. "Synthetic Technics of Methyl Acrylate through Aldol Condensation with a Multisubsection Fixed-Bed Reactor." Advanced Materials Research 233-235 (May 2011): 2859–62. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.2859.

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Two types of catalysts, V2O5-P2O5/SiO2and Cs-Sb2O5/SiO2, were separately prepared with SiO2as carrier. Their catalytic properties were investigated in the process of synthesizing methyl acrylate through aldol condensation with methylal and methyl acetate, and the influence of the catalyst’s filling up technique on the reaction was studied. Reactions were performed in a fixed-bed reactor. The research results indicate that aldol condensation reaction is effectively promoted when the two catalysts were filled up in appropriate subsections of the reaction tube. Specifically, when V-Si-P Oxide was
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42

Anderson, Oren P., Anthony GM Barrett, Jeremy J. Edmunds, et al. "Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A." Canadian Journal of Chemistry 79, no. 11 (2001): 1562–92. http://dx.doi.org/10.1139/v01-133.

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The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, a
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43

Bercich, Mark D., Richard C. Cambie, and Peter S. Rutledge. "Experiments Directed Towards the Synthesis of Anthracyclinones. XXXIV Hetero-Diels - Alder Reactions Using Chiral Boron and Titanium Reagents." Australian Journal of Chemistry 52, no. 9 (1999): 851. http://dx.doi.org/10.1071/ch98181.

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Reactions between benzaldehyde or o-anisaldehyde and a series of silyloxy dienes catalysed by the chiral acyl- oxyborane (CAB) complex (4) give high yields of enantioselective products from a Mukaiyama aldol rather than a hetero-Diels–Alder reaction. Attempts to effect a similar catalytic reaction with anthraquinone aldehydes were unsuccessful but use of 2 equiv. of the CAB complex (1) followed by cyclization promotes a formal hetero- Diels–Alder reaction between the aldehyde (7) and the diene (12) to give the dihydropyrone (24) in 45% yield and with a 79% e.e. in favour of the 2'R enantiomer.
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44

Ghosh, Arun K., and Jae-Hun Kim. "Ester derived titanium enolate aldol reaction: chelation controlled diastereoselective synthesis of syn -aldols." Tetrahedron Letters 42, no. 7 (2001): 1227–31. http://dx.doi.org/10.1016/s0040-4039(00)02227-9.

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45

Konrad, David, Bilal Kicin, and Dirk Trauner. "Concise Asymmetric Synthesis of Kweichowenol A." Synlett 30, no. 04 (2018): 383–86. http://dx.doi.org/10.1055/s-0037-1610390.

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An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.
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46

Inoue, Tadashi, Ji-Feng Liu, Dana C. Buske, and Atsushi Abiko. "Boron-Mediated Aldol Reaction of Carboxylic Esters: Complementary Anti- and Syn-Selective Asymmetric Aldol Reactions." Journal of Organic Chemistry 67, no. 15 (2002): 5250–56. http://dx.doi.org/10.1021/jo0257896.

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47

Listratova, Anna, and Leonid Voskressensky. "Recent Advances in the Synthesis of Hydrogenated Azocine-Containing­ Molecules." Synthesis 49, no. 17 (2017): 3801–34. http://dx.doi.org/10.1055/s-0036-1589500.

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This review covers recent advances in synthesis of azocine-containing systems. The most approaches towards azocines are discussed.1 Introduction2 Ring-Expansion Reaction2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines (from 5 to 8)2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines under the Action of Activated Alkynes (from 6 to 8)2.3 Reductive Ring-Expansion Reaction of Cyclic Oximes2.4 Other Ring-Expansion Reactions3 Heck Reaction4 Cycloaddition5 Ring-Closing Metathesis (RCM)6 Cyclization6.1 Metal-Catalyzed Cyclization6.2 Radical Cy
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48

Juaristi, Eusebio, Carlos Cruz-Hernández, and Perla Hernández-González. "(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organo­catalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water." Synthesis 50, no. 09 (2018): 1827–40. http://dx.doi.org/10.1055/s-0036-1591916.

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Novel organocatalysts derived from (R)- and (S)-proline and incorporating a chiral phosphoramide fragment were rationally designed and subsequently synthesized. These chiral compounds catalyze the enantioselective aldol addition reaction of cyclohexanone to prochiral isatins in the presence of water. These observations are particularly relevant since reports of asymmetric aldol reactions between cyclohexanone­ and isatins catalyzed by chiral secondary amines remain scarce, with primary amines being the most studied and successful catalysts. The present report includes a thorough evaluation of
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49

Xiang, YiBin, Eric Olivier, and Nathalie Ouimet. "Stereoselective aldol reactions. Reaction of chiral ester titanium enolate with aldehydes." Tetrahedron Letters 33, no. 4 (1992): 457–60. http://dx.doi.org/10.1016/s0040-4039(00)93967-4.

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50

Conley, Mark, Mike Mojica, Fiaz Mohammed, et al. "Reaction of glycine with glyoxylate: Competing transaminations, aldol reactions, and decarboxylations." Journal of Physical Organic Chemistry 30, no. 12 (2017): e3709. http://dx.doi.org/10.1002/poc.3709.

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