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Relevant bibliographies by topics / Aldol condensation reaction

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Academic literature on the topic 'Aldol condensation reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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Journal articles on the topic "Aldol condensation reaction"

1

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 (March 15, 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 to crotonaldehyde was favored at temperatures below 300oC. It has also been suggested that both Brønstedand Lewis acids are involved in aldol reactions with Lewis acid sites the most probable catalytic sites. The zeolite group of minerals has founduse in many chemical and allied industries.DOI: http://dx.doi.org/10.3126/ijasbt.v3i1.12291 Int J Appl Sci Biotechnol, Vol. 3(1): 1-8

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Witzig, Reto M., and Christof Sparr. "Synthesis of Enantioenriched Tetra-ortho-3,3′-substituted Biaryls by Small-Molecule-Catalyzed Noncanonical Polyketide Cyclizations." Synlett 31, no. 01 (October 22, 2019): 13–20. http://dx.doi.org/10.1055/s-0039-1690215.

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The arene-forming aldol condensation is a fundamental reaction in the biosynthesis of aromatic polyketides. Precisely controlled by the polyketide synthases, the highly reactive poly-β-carbonyl substrates are diverged into numerous aromatic natural products by selective cyclization reactions; a fascinating biosynthetic strategy that sparked our interest to investigate atroposelective aldol condensations. In this Account, we contextualize and highlight the ability of small-molecule catalysts to selectively convert noncanonical hexacarbonyl substrates in a double arene-forming aldol condensation resulting in the atroposelective synthesis of tetra-ortho-3,3′-substituted biaryls. The hexacarbonyl substrates were obtained by a fourfold ozonolysis enabling a late-stage introduction of all carbonyl functions in one step. Secondary amine catalysts capable of forming an extended hydrogen-bonding network triggered the noncanonical polyketide cyclization in order to form valuable biaryls in high yields and with stereocontrol of up to 98:2 er.1 Biosynthesis of Aromatic Polyketides2 Rotationally Restricted Aromatic Polyketides3 3,3′-Substituted Binaphthalenes in Catalysis4 Stereoselective Synthesis of Atropisomers5 Synthesis of Enantioenriched Tetra-ortho-3,3′-Substituted Biaryls by the Atroposelective Arene-Forming Aldol Condensation6 Conclusion

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Raston, Colin L., and Janet L. Scott. "Chemoselective, solvent-free aldol condensation reaction." Green Chemistry 2, no. 2 (2000): 49–52. http://dx.doi.org/10.1039/a907688c.

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Eskendirov, Igor, Bukasa Kabongo, Leslie Glasser, and Valery D. Sokolovskii. "Kinetics by thermometry: an aldol condensation reaction." Journal of the Chemical Society, Faraday Transactions 91, no. 6 (1995): 991. http://dx.doi.org/10.1039/ft9959100991.

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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 (June 21, 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 multifunctional catalyst containing Mg, Ru and Al was prepared by coprecipitation and hydrothermal treatment. The catalyst was characterized by elemental analysis, Powder XRD, FT-IR, BET, TGA, DRS, SEM, EDX, XPS and TEM. The products of the reactions were characterized by 1H NMR and GC-MS. Results: The analysis of catalyst revealed incorporation of Ru in the brucite layers of the LDH and showed the mosaic single crystal with BET surface area of 84.25 m2 g-1. This catalyst yielded 85–98% products for Aldol condensation reactions within 4 h reaction time, and 82–98% products for transfer hydrogenation reactions within 16 h reaction time. Conclusion: The resultant MgRuAl-LDH with acid and base sites was found to be highly active and selective for one-step synthesis of nitrile compounds. The catalyst works more efficiently for Aldol condensation reactions in shorter reaction times compared to transfer hydrogenation reactions.

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Thongnuam, Worawaran, Suwapich Pornsatitworakul, Thana Maihom, Piti Treesukol, Nongpanga Jarussophon, Phornphimon Maitarad, Kanokwan Kongpatpanich, and Bundet Boekfa. "An Experimental and Theoretical Study on the Aldol Condensation on Zirconium-Based Metal-Organic Framework." Key Engineering Materials 757 (October 2017): 98–102. http://dx.doi.org/10.4028/www.scientific.net/kem.757.98.

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The aldol condensation of acetone in zirconium-based metal-organic framework functionalized by a sulfonic acid group (UiO-66-SO3H) has been theoretically investigated using the density functional theory. Acetone adsorbed on the UiO-66-SO3H with the adsorption energy of -17.4 kcal/mol. The catalyzed reaction has been proposed to be a two-step mechanism: the tautomerization of keto form to produce enol form of acetone, and the aldol condensation to produce diacetone alcohol. The activation energies were calculated to be 27.2 and 6.4 kcal/mol, respectively. For the experimental part, UiO-66-SO3H catalyst was synthesized and characterized by X-ray diffraction and IR spectroscopy. The catalytic reaction was carried out in a stirred batch reactor at different temperatures to optimize the reaction conditions. The obtained products were analyzed by 1H-NMR spectroscopy and chromatography techniques. This study demonstrated that UiO-66-SO3H can be used as a solid catalyst for the aldol condensation reaction.

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Zhang, Ya-Fei, Shao-Jie Yin, Min Zhao, Jun-Qi Zhang, Hai-Yan Li, and Xing-Wang Wang. "Dinuclear zinc-catalyzed desymmetric intramolecular aldolization: an enantioselective construction of spiro[cyclohexanone-oxindole] derivatives." RSC Advances 6, no. 36 (2016): 30683–89. http://dx.doi.org/10.1039/c6ra02296k.

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A bis-ProPhenol zinc complex-catalyzed asymmetric desymmetrizing intramolecular aldol or aldol condensation reaction is reported, which furnishes spiro[cyclohexanone-oxindole] derivatives in good yields with moderate to high enantioselectivities.

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Abedi, Sedigheh, Alireza Azhdari Tehrani, Hosein Ghasempour, and Ali Morsali. "Interplay between hydrophobicity and basicity toward the catalytic activity of isoreticular MOF organocatalysts." New Journal of Chemistry 40, no. 8 (2016): 6970–76. http://dx.doi.org/10.1039/c6nj00480f.

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Dreier, Anna-Lena, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes." Beilstein Journal of Organic Chemistry 14 (February 8, 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 esters were produced. The reaction was also successful with meta-substituted benzaldehydes and o-fluorobenzaldehyde. In contrast, p-methyl-, p-methoxy-, and p-ethoxybenzaldehydes led selectively to aldol condensation products with (E)-configured double bonds in 30–40% yields. In preliminary experiments with an SF5-substituted acetic acid morpholide and p-nitrobenzaldehyde, a low amount of an aldol product was formed under similar conditions.

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Nagumo, Shinji, Aki Matsukuma, Fumiko Inoue, Takayoshi Yamamoto, Hiroshi Suemune, and Kiyoshi Sakai. "Ring cleavage reaction based on intermolecular aldol condensation." Journal of the Chemical Society, Chemical Communications, no. 21 (1990): 1538. http://dx.doi.org/10.1039/c39900001538.

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Dissertations / Theses on the topic "Aldol condensation reaction"

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Liu, Jing. "Synthesis of resveratrol and its analogs, phase-transfer catalyzed asymmetric glycolate aldol reactions, and total synthesis of 8,9-methylamido-geldanamycin /." Diss., CLICK HERE for online access, 2007. http://contentdm.lib.byu.edu/ETD/image/etd1998.pdf.

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Wang, Zheng. "Preparation and Characterization of Rare Earth Elements Modified Hydrotalcites and Their Catalytic Performances for Aldol Condensation Reactions." Thesis, Lyon 1, 2015. http://www.theses.fr/2015LYO10091.

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Résumé anglais uniquement
Nowadays there is an urgent need to develop green chemical processes, where the use and generation of toxic substances can be avoided. Indeed, the lignocellulose feedstock destructuration will produce aqueous solutions of ketones or aldehydes and it would be an important breakthrough to develop solid base catalysts capable to promote the aldol condensation. In this thesis, the main results are shown as follows: Magnesium and rare earth mixed oxides (MgReOx), rare earth modified MgAl-HT catalyst were prepared and were evaluated in liquid phase acetone self-aldolization. Rare earth modified MgAl catalysts show enhanced catalystic activity than MgReOx catalysts. Rehydrated MgAl-HT modified with Y and La, also present a higher water tolerance for aldol reaction. The same catalysts were also applied to acetone gas phase self-condensation reaction. At low temperature, the mesityl oxide is the main product for all the catalysts. At high temperatures, deactivation rate is lowered over MgAlCe(Y)O catalysts, and the presence of trimers (selectivity of IP over 50%) is much more noticeable for the MgAlY(Ce)O catalysts. A good balance between basicity and acidity is proposed to increase the selectivity of IP. In the cross condensation of citral and acetone, the citral conversion and pseudoionone yield were significantly enhanced over Mg3AlaY1-aOx catalysts. A general mechanism of reaction was proposed that the Y modified MgAl mixed oxides undergoes the rehydration by the water formed during the reaction, and the rehydrated catalysts with active Brønsted basic sites are responsible for the significantly improvement of catalytic activity

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Hameed, Ahmed. "Development of chromatographic methods to follow heterogeneous organic chemistry in aerosols." Thesis, University of Manchester, 2016. https://www.research.manchester.ac.uk/portal/en/theses/development-of-chromatographic-methods-to-follow-heterogeneous-organic-chemistry-in-aerosols(8a646675-d94c-4064-83d0-af11df225ac5).html.

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Atmospheric aldol self-reactions of octanal, heptanal and hexanal in a range of aqueous H2SO4 w/v% concentrations as a catalyst were studied in both bulk liquid-liquid experiments and gas-liquid experiments. Initially, a new practical methodology was developed and enhanced to monitor aldol reactions in aqueous acidic media. The evaluation of a quenching and extracting method were performed, confirming the suitability, reliability and reproducibility of the extraction method. In bulk studies, aldol products of the three aldehydes were separated and identified by preparative HPLC, GC-MS and NMR. The major aldol products observed at high acid concentrations were alpha,β-unsaturated aldehyde (dimer), trialkyl benzene (trimer) and tetraalkylcycloocta-tetraene (tetramer). The trimer of octanal was formed as trioxane in low sulfuric acid concentration and the possible mechanism accretion reaction pathways of high and low acid concentrations are proposed in this study. A systematic kinetic study of octanal, heptanal and hexanal in the bulk experiments at 65, 60 and 55 w/v% H2SO4 at 294 K were monitored using gas chromatographic equipped with a flame ionisation detector (GC-FID). The rate constants were generally estimated using second order kinetics and observed to increase as a function of sulfuric acid concentrations and also as the chain length of aliphatic aldehyde increased. The aldol self-reaction in the bulk experiment was too fast at room temperature to be easily measured using a quenching method therefore attempts were made to follow the reaction at low temperature (0 °C). The result at low temperature indicated that the rate constant of aldehyde was reduced but there was an issue of rapid rise in temperature as a result of mixing concentrated sulfuric acid with aqueous solution of the aldehyde. A gas bubbling system was developed which better simulates atmospheric reality, and which also resolves the issue of temperature rise on mixing. Two different methodologies were used: one in which the aldehyde was continually added, and one where a fixed amount was added from the gas phase and the reaction was then allowed to proceed, monitored at selected time intervals. The precision and accuracy of the fixed method was then further improved by the addition of an internal standard (IS). Using this, the concentrations of aliphatic aldehydes (C6-C8) were calibrated using an experimentally determined response factor and used to follow the loss of the reactant aldehydes. Similar methods were applied to the aldol dimers (C6-C8), which were purified and used to calibrate the chromatographic response. The rate constant for octanal, heptanal and hexanal at 76 wt% and 294 K were 0.0969 M-1 s-1, 0.1497 M-1 s-1 and 0.2622 M-1 s-1 respectively. There are some observations based upon the results presented in this thesis that may be of atmospheric significance: (i) phase separation between organic and aqueous layers in both the bulk experiment and in the bubbling system; (ii) the acid strength dependence and concentration-dependence of the various products; (iii) the faster rates than previously reported, and variation between bulk and bubbling; and (v) the time-dependent colour changes. Further work to explore these observations is proposed.

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Cassaro, Rafael Frascino. "Organocatálise em CO2 supercrítico: reatividade e otimização de processo." Universidade de São Paulo, 2015. http://www.teses.usp.br/teses/disponiveis/46/46136/tde-20072015-112951/.

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O dióxido de carbono no estado supercrítico (CO2-SC) tem despertado considerável interesse nos últimos anos como um novo solvente para reações orgânicas. Nesta tese foi investigada a influência do uso de CO2 supercrítico, associado ou não a líquidos iônicos ou cossolventes, como solvente em reações químicas visando à obtenção de precursores quirais. Foram estudadas as reações de condensação Aldólica, de Morita-Baylis-Hillman (MBH) e do tipo adição de Michael, empregando Organocatálise quando conveniente, isto é, catalisadores provenientes de aminoácidos e ácidos carboxílicos. As reações de MBH foram otimizadas através de um planejamento experimental e sua condição ótima se deu a 70°C, 110 bar, com 6 equivalentes de H2O, tempo reacional de 2h30 min e sem a presença de liquido iônico, tendo um rendimento de 84,6%. Para as condensações aldólicas os melhores resultados com acetona e p-nitrobenzaldeido como materiais de partida foram obtidos a 150 bar e 40°C, com a presença de liquido iônico, em 2 horas de tempo reacional com um rendimento de 54,0% e um excesso enantiomérico de 79,0% utilizando o catalisador (2S,4R)-4-(terc-butildimetilsililoxi)pirrolidina-2-ácido carboxílico. Com ciclohexanona como material de partida foram obtidos a 150 bar e 40°C com a presença de um doador de prótons (resina de troca iônica) em 2 horas de tempo reacional com um rendimento de 70,9% e um excesso enantiomérico de 91,2%, utilizando o catalisador (2S,4R)-4-(terc-butildimetilsililoxi)pirrolidina-2-ácido carboxílico. Outros aldeídos e cetonas utilizados como materiais de partida apresentaram rendimentos menores. Estudos de comportamento de fases foram feitos para os materiais de partida, catalisadores e produtos da reação de condensação Aldólica. Os melhores rendimentos foram obtidos em situações em que os materiais de partida e os catalisadores eram solúveis na fase supercrítica, mas os produtos não, formando uma segunda fase.
Supercritical carbon dioxide (sc-CO2) has attracted considerable interest in the last years as a new solvent for organic reactions. In this thesis, the influence of supercritical CO2 use, associated or not to ionic liquids or cosolvents, as a solvent for chemical reactions aiming at the synthesis of chiral precursors was studied. Aldol condensation, Morita-Baylis-Hillman (MBH) and Michael addition reactions were studied, employing organocatalysis when it was convenient, i.e., catalysts derived from aminoacids or carboxylic acids. MBH reactions were optimized through experimental design, resulting in a maximum yield of 84.6% for the optimal condition at 70°C, 110 bar, and 6 equivalents of H2O, reaction time of 2h30 min and the absence of ionic liquids. For the Aldol condensation reactions employing acetone and p-nitrobenzaldehyde, a maximum yield of 54.0%, with an enantiomeric excess of 79.0% was obtained at 150 bar, 40°C, 2h reaction time, in the presence of ionic liquid, using the catalyst (2S,4R)-4-(terc-butyldimethylsililoxy)pirrolidine-2-carboxylic acid. The yields were significantly lower for other aldehydes and ketones. Yields for Michael addition reactions were very low and their study was discontinued. Phase behavior studies were performed with starting materials, catalysts and products for the Aldol condensation reactions. The best yields were obtained for situations where the starting materials and catalysts were soluble in the supercritical phase and the products were not, forming a second phase.

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HOUTTEVILLE, MARIE-CLAIRE. "Etude de la simple et de la double diastereoselectivite de la reaction d'aldolisation de l'acide propanedithioique : synthese de beta-oxodithioesters par oxydation chimioselective de beta-hydroxydithioesters." Caen, 1988. http://www.theses.fr/1988CAEN2006.

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SEGUINEAU, PASCALE. "Les reactions de wittig et wittig-horner en milieu protique peu basique." Nantes, 1989. http://www.theses.fr/1989NANT2014.

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La reaction de wittig-horner realisee dans des conditions douces (milieu aqueux peu basique) a l'aide de composes dicarbonyles permet d'acceder par bisaldolisation a des cyclenols alpha -fonctionnalises. Grace a cette technique douce, la reaction de wittig-horner est chimioselective et ne s'effectue que sur les sites carbonyles tres actifs (aldehydes)

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CASTANY, MARIE-HELENE. "Les triflates du germanium en synthese organometallique et organique." Toulouse 3, 1998. http://www.theses.fr/1998TOU30267.

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Cette these presente la synthese et la reactivite de triflates du germanium en tant qu'agents de germylation et catalyseur acide de lewis. Le premier chapitre decrit plusieurs voies de synthese de mono- et ditriflates du germanium par action de l'acide triflique sur differents composes organomettaliques. Le deuxieme chapitre est consacre a la germylation de nombreuses fonctions organiques a partir des triflates du germanium ou de chlorogermanes. Pour ces deux voies de synthese, une etude mecanistique est menee afin d'interpreter la regiochimie et la stereochimie de la germylation. Le troisieme chapitre met en evidence l'activite catalytique des triflates germanies en tant qu'acide de lewis dans la reaction d'aldolisation croisee entre les enols o- et c- germanies et un aldehyde, un acetal ou une imine. La diastereoselectivite observee pour ces reactions a pu etre interpretee a partir d'un mecanisme d'approche a interactions steriques et electrostatiques minimales faisant intervenir des etats de transitions ouverts ou cycliques. La reaction de friedel et crafts, sous catalyse par le triflate de trimethylgermanium, fait l'objet du dernier chapitre.

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Riss, Bernard. "Substances antiappetantes pour insectes phytophages : synthese totale de la bisabolangelone." Université Louis Pasteur (Strasbourg) (1971-2008), 1987. http://www.theses.fr/1987STR13030.

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Dans le cadre des substances antiappetantes pour insectes phytophages, nous presentons la premiere synthese totale de la bisabolangelone. Il s'agit d'un antiappetant sesquiterpenoide, present dans angelica silvestris. La strategie de synthese, fait appel a une reaction tres peu exploitee : l'additioon intramoleculaire d'un alcool sur une triple liaison. Cette reaction permet d'acceder au motif (methyl-3 butene-2 ylidene)-2 tetrahydrofuranne de facon stereospecifique. Dans un premier temps, l'etude d'un modele nous a permis de connaitre la versatilite et les limites d'application de cette reaction. Apres plusiurs tentatives infructueuses, nous sommes parvenus au produit cible. Au cours de cette synthese, nous avons ete confrontes aux reactions suivantes : aldolisations ; additions de lithiens acetyleniques ; cycloadditions 1-3 dipolaires ; protections et deprotection selectives de polyols

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Hamelin, Olivier. "Synthèses du (+)- et du (-)-9-acétoxyfukinanolide : Synthèse du (+)-dihydrofukinolidol, intermédiaire central des bakkénolides difonctionnalisés." Université Joseph Fourier (Grenoble ; 1971-2015), 1997. http://www.theses.fr/1997GRE10155.

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Depuis bien une dizaine d'annees, une des activites de notre laboratoire est le developpement de nouvelles methodologies de synthese en vue d'acceder efficacement a une famille de composes particuliers que sont les bakkanes. Ils sont caracterises par la presence d'un squelette hydrindanique et d'une spiro, methylene, butyrolactone qui est a l'origine des activites biologiques tres diverses des bakkanes. Notre laboratoire avait developpe une approche souple et efficace des spirolactones hydrindaniques. Elle avait permis la synthese du ()- et du (+)-bakkenolide-a, du ()-homogynolide-b, du ()- et du (-)-homogynolide-a et du ()-palmosalide-c mais s'est averee infructueuse pour la synthese du 9-acetoxyfukinanolide. Au cours de ce travail, nous avons realise les premieres syntheses du ()- et du (-)-9-acetoxyfukinanolide avec une totale stereoselectivite. Notre strategie fait intervenir 3 etapes cles dont la formation du squelette hydrindanique par expansion de cycle, la formation de la spirolactone par cyclisation radicalaire d'un -cetoester propargylique par le mn(iii) et une reaction de retroaldol-aldolisation qui permet d'acceder a la stereochimie des bakkanes naturels. A partir d'un intermediaire cle de cette synthese, nous avons pu acceder rapidement au dihydrofukinolidol, bakkane non naturel, intermediaire central des bakkenolides difonctionnalises. Ce travail nous a permis par ailleurs, de developper une nouvelle methodologie de formation d'-acyl, methylene, butyrolactones par cyclisation radicalaire de -cetoesters propargyliques obtenus par transesterification en milieu neutre de -cetoesters methyliques.

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Puchot, Catherine. "Contribution à l'étude des synthèses asymétriques catalysées par les acides aminés." Paris 6, 1986. http://www.theses.fr/1986PA066136.

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Books on the topic "Aldol condensation reaction"

1

Mahrwald, Rainer. Aldol Reactions. Dordrecht: Springer Netherlands, 2009.

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Fish, Joshua. Pyrite as a catalyst for aldol condensation reactions. Sudbury, Ont: Laurentian University, 2001.

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A, Evans David, and Rainer Mahrwald. Modern Aldol Reactions. Wiley & Sons, Limited, John, 2008.

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Mahrwald, Rainer. Modern Methods in Stereoselective Aldol Reactions. Wiley & Sons, Incorporated, John, 2013.

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Mahrwald, Rainer. Modern Methods in Stereoselective Aldol Reactions. Wiley & Sons, Incorporated, John, 2013.

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Mahrwald, Rainer. Modern Methods in Stereoselective Aldol Reactions. Wiley & Sons, Limited, John, 2013.

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Mahrwald, Rainer. Modern Methods in Stereoselective Aldol Reactions. Wiley & Sons, Incorporated, John, 2013.

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Modern Methods In Stereoselective Aldol Reactions. Wiley-VCH Verlag GmbH, 2013.

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David A. Evans (Foreword, Editor) and Rainer Mahrwald (Editor Foreword), eds. Modern Aldol Reactions (2 Volume Set). Wiley-VCH, 2004.

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Laci, Michelle Ann. The design and synthesis of a chiral auxiliary for use in Diels-Alder cycloaddtions and aldol condensation reactions. UMI, 1998.

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Book chapters on the topic "Aldol condensation reaction"

1

Li, Jie Jack. "Aldol condensation." In Name Reactions, 3–5. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_2.

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Li, Jie Jack. "Aldol condensation." In Name Reactions, 3–5. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_2.

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Li, Jie Jack. "Aldol condensation." In Name Reactions, 3. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_3.

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Li, Jie Jack. "Aldol Condensation." In Name Reactions, 4–6. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_2.

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Paterson, Ian. "Aldol Condensations of Ketones Using Chiral Boron Reagents." In Selectivities in Lewis Acid Promoted Reactions, 311. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2464-2_24.

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Wachter, Nanette M. "Using NMR To Investigate Products of Aldol Reactions: Identifying Aldol Addition versus Condensation Products or Conjugate Addition Products from Crossed Aldol Reactions of Aromatic Aldehydes and Ketones." In ACS Symposium Series, 91–102. Washington, DC: American Chemical Society, 2013. http://dx.doi.org/10.1021/bk-2013-1128.ch007.

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Fallis, A. G., and M. S. Souweha. "Aldol Condensation Reaction." In Polyynes, Arynes, Enynes, and Alkynes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-043-00236.

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8

Li, Jie Jack, Chris Limberakis, and Derek A. Pflum. "Carbon−Carbon Bond Formation." In Modern Organic Synthesis in the Laboratory. Oxford University Press, 2008. http://dx.doi.org/10.1093/oso/9780195187984.003.0011.

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Reviews: (a) Vicarion, J. L.; Badia, D.; Carillo, L.; Reyes, E.; Etxebarria, J. Curr. Org. Chem. 2005, 9, 219-235. (b) Mahrwald, R. Ed. In Modern Aldol Reactions; Wiley-VCH: Weinheim, 2004; Vol. 1., pp. 1-335 (c) Mahrwald, R. Ed. In Modern Aldol Reactions; Wiley-VCH: Weinheim, 2004; Vol. 2., pp. 1-345.(d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352-1375. (e) Carriera, E. M. In Modern Carbonyl Chemistry; Otera, J.; Wiley-VCH: Weinheim, 2000; Chapter 8: Aldol Reaction: Methodology and Stereochemistry, 227-248. (f) Paterson, I.; Cowden, C. J.; Wallace, D. J. In Modern Carbonyl Chemistry; Otera, J.; Wiley-VCH: Weinheim, 2000; Chapter 9: Stereoselective Aldol Reactions in the Synthesis of Polyketide Natural Products, pp. 249-298. (g) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1 317-338. (h) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, Fl.; 1984; Vol. 3., Chapter 2: The Aldol Addition Reaction, pp. 111-212. (i) Mukaiyama, T. Org. React. 1982, 28, 203-331. Since the early 1980s, aldol condensations involving boron enolates have gain great importance in asymmetric synthesis, particularly the synthesis of natural products with adjacent stereogenic centers bearing hydroxyl and methyl groups. (Z)-Boron enolates tend to give a high diastereoslectivity preference for the syn-stereochemistry while (E)-boron enolates favor the anti-stereochemistry. Because the B-O and B-C bonds are shorter than other metals with oxygen and carbon, the six membered Zimmerman–Traxler transition state in the aldol condensation tends to be more compact which accentuates steric interactions, thus leading to higher diastereoselectivity. When this feature is coupled with a boron enolate bearing a chiral auxillary, high enantioselectivity is achieved. Boron enolates are generated from a ketone and boron triflate in the presence of an organic base such as triethylamine. Reviews: (a) Abiko, A. Acc. Chem. Res. 2004, 37, 387-395. (b) Cowden, C. J. Org. React. 1997, 51, 1-200.

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9

Taber, Douglass F. "The Bradshaw/Bonjoch Synthesis of (-)-Anominine." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0097.

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The Hajos-Parrish cyclization was a landmark in the asymmetric construction of polycarbocyclic natural products. Impressive at the time, the proline-mediated intramolecular aldol condensation proceeded with an ee that was low by modern standards. Ben Bradshaw and Josep Bonjoch of the Universitat de Barcelona optimized this protocol, then used it to prepare (J. Am. Chem. Soc. 2010, 132, 5966) the enone 3 en route to the Aspergillus alkaloid (-)-anominine 4. The optimized catalyst for the enantioselective Robinson annulation was the amide 5 . With 2.5 mol % of the catalyst, the reaction proceeded in 97% ee. With only 1 mol % of catalyst, the reaction could be taken to 96% yield while maintaining the ee at 94%. Conjugate addition proceeded across the open face of 3 to give, after selective protection, the monoketal 7. After methylenation and deprotection, oxidation with IBX delivered the enone 9. With the angular quaternary centers of the natural product in place, the molecule became increasingly congested. Attempted direct alkylation of 9 led mainly to O-methylation. A solution to this problem was found in condensation with the Eschenmoser salt, followed by N-oxide formation and elimination to give the tetraene 10. Selective reduction by the Ganem protocol followed by equilibration completed the net methylation. Under anhydrous conditions, the oxide derived from the allylic selenide 12 did not rearrange. On the addition of water, the rearrangement proceeded smoothly. Protection and hydroboration converted 13 into 14. The bulk of the folded molecule protected the exo methylene of 14, so hydrogenation followed by protection and oxidation delivered 15. Conjugate addition of indole to 15 set the stage for oxidation and bis-methylenation to give 17. Selective Ru-mediated cross-coupling with 18 followed by deprotection then completed the synthesis of (-)-anominine 4, which proved to be the enantiomer of the natural product.

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10

Taber, Douglass F. "Arrays of Stereogenic Centers: The Yadav Synthesis of Nhatrangin A." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0040.

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Miquel Costas of the Universitat de Girona developed (J. Am. Chem. Soc. 2013, 135, 14871) an iron catalyst for the enantioselective epoxidation of the Z-ester 1 to 2. Although the α-chloro aldehyde derived from 3 epimerized under the reaction conditions, Robert Britton of Simon Fraser University showed (Org. Lett. 2013, 15, 3554) that the subsequent aldol condensation with 4 favored one enantiomer, leading to 5 in high ee. Other selective aldol condensations of 4 (not illustrated) have been reported by Zorona Ferjancic and Radomir N. Saicic of the University of Belgrade (Eur. J. Org. Chem. 2013, 5555) and by Tomoya Machinami of Meisei University (Synlett 2013, 24, 1501). Motomu Kanai of the University of Tokyo condensed (Org. Lett. 2013, 15, 4130) D-arabinose 6 with diallyl amine and the alkyne 7 to give the amine 8 as a mixture of diastereomers. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry combined (Angew. Chem. Int. Ed. 2013, 52, 7310) 9 and 10 to prepare the α-chiral amine 11. Tomoya Miura and Masahiro Murakami of Kyoto University used (J. Am. Chem. Soc. 2013, 135, 11497) an Ir catalyst to migrate the alkene of 13 to the E allyl boronate, that then added to 12 to give 14. Gong Chen of Pennsylvania State University alkylated (J. Am. Chem. Soc. 2013, 135, 12135) the β-H of 15 with 16 to give selectively the diastereomer 17. Geoffrey W. Coates of Cornell University devised (J. Am. Chem. Soc. 2013, 135, 10930) catalysts for the carbonylation of the epoxide 18 to either regioisomer of the β-lactone 19. Yujiro Hayashi of Tohoku University combined (Chem. Lett. 2013, 42, 1294) the inexpensive succinaldehyde 20 and ethyl glyoxylate 21 to give the versatile aldehyde 22. Nuno Maulide of the Max-Planck-Institut für Kohlenforschung Mülheim effected (J. Am. Chem. Soc. 2013, 135, 14968) Claisen rearrangement of 23 to give, after reduction and hydrolysis, the aldehyde 24. Stephen G. Davies of the University of Oxford reported (Chem. Commun. 2013, 49, 7037) a related Claisen rearrangement (not illustrated). Ying-Chun Chen of Sichuan University devised (Org. Lett. 2013, 15, 4786) the cascade combination of 25 and 26 to give 27.

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Conference papers on the topic "Aldol condensation reaction"

1

Cahyana, A. H., B. Ardiansah, and M. B. Maloka. "Magnetite - activated chicken eggshell (Fe3O4-ACE) composite for aldol condensation reaction." In PROCEEDINGS OF THE 3RD INTERNATIONAL SYMPOSIUM ON CURRENT PROGRESS IN MATHEMATICS AND SCIENCES 2017 (ISCPMS2017). Author(s), 2018. http://dx.doi.org/10.1063/1.5064075.

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2

Nebesnyi, Roman, Volodymyr Ivasiv, Iryna Shpyrka, Yuliia Nebesna, Volodymyr Sydorchuk, and Svitlana Khalameida. "Synthesis of acrylic acid via aldol condensation reaction on titanium and mixed vanadium-titanium phosphate catalysts with different porous structure." In 2017 IEEE 7th International Conference "Nanomaterials: Application & Properties" (NAP). IEEE, 2017. http://dx.doi.org/10.1109/nap.2017.8190167.

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3

SASAKI, M., T. HAYAKAWA, K. ARAI, and T. ADSCHIRI. "MEASUREMENT OF THE RATE OF RETRO-ALDOL CONDENSATION OF D-XYLOSE IN SUBCRITICAL AND SUPERCRITICAL WATER." In Proceedings of the Seventh International Symposium on Hydrothermal Reactions. WORLD SCIENTIFIC, 2003. http://dx.doi.org/10.1142/9789812705228_0022.

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4

El-Molla, Sahar, and Hala Mahmoud. "The Effect of Transition Metal Oxide Dopants on the Structure, Morphology, Surface Texture and Catalytic Properties of FeMgO Nanomaterials Towards Dehydrogenation and Aldol Condensation Reactions." In The 19th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2015. http://dx.doi.org/10.3390/ecsoc-19-a055.

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