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Journal articles on the topic 'Aldol Reaction'

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Published: 4 June 2021

Last updated: 25 April 2022

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1

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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2

Schreyer, Lucas, Philip S. J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, and Benjamin List. "Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates." Science 362, no. 6411 (October 11, 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 developed, strongly acidic imidodiphosphorimidates (IDPi), which, like enzymes, display a confined active site but, like small-molecule catalysts, have a broad substrate scope. The process is scalable, fast, efficient (0.5 to 1.5 mole % catalyst loading), and greatly simplifies access to highly valuable silylated acetaldehyde aldols.

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3

Jung, Michael E., and Alexandra van den Heuvel. "A Tandem Non-Aldol Aldol Mukaiyama Aldol Reaction." Organic Letters 5, no. 24 (November 2003): 4705–7. http://dx.doi.org/10.1021/ol0358760.

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4

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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5

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 (March 1, 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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6

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 (August 1, 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 substituents and substituent positions with reduced electron withdrawing effects on the borate function. Optimal suppression of the dehydration of β-hydroxyketones was obtained for compounds corresponding to phenylboronic acids with a pKa > 7. The reactions between benzaldehyde and butanone or 3-pentanone did not show diastereoselectivity, which suggests that the catalysts merely act as bases rather than as templates for the transition state of the aldol reaction. Sterically more demanding ketones were not converted.

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7

Cordes, Martin, and Markus Kalesse. "Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis." Molecules 24, no. 17 (August 22, 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 vinylogous Mukaiyama aldol reaction (VMAR) became a pivotal transformation as it allows the synthesis of larger fragments while incorporating 1,5-relationships and generating two new stereocenters and one double bond simultaneously. This review summarizes and updates methodology-oriented and target-oriented research focused on the various aspects of the vinylogous Mukaiyama aldol (VMA) reaction. This manuscript comprehensively condenses the last four years of research, covering the period 2016–2019.

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8

Ju, Longxin, Gang Li, and Hongxian Luo. "Catalytic Synthesis of Methacrolein via the Condensation of Formaldehyde and Propionaldehyde with L-Proline Intercalated Layered Double Hydroxides." Catalysts 12, no. 1 (December 31, 2021): 42. http://dx.doi.org/10.3390/catal12010042.

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Aldol condensation reactions are very important C–C coupling reactions in organic chemistry. In this study, the catalytic performance of layered double hydroxides (LDHs) in the aldol condensation reaction of formaldehyde (FA) and propionaldehyde (PA) was investigated. The MxAl-LDHs (denoted as re-MxAl–LDHs; M = Ca and Mg; X = 2–4), as heterogeneous basic catalysts toward the aldol condensation reaction, were prepared via a two-step procedure. The catalyst exhibited a high PA conversion (82.59%), but the methacrolein (MAL) selectivity was only 36.01% due to the limitation of the alkali-catalyzed mechanism. On this basis, the direct intercalation of L-proline into LDHs also has been investigated. The influences of several operating conditions, including the temperature, reaction time, and substrate content, on the reaction results were systematically studied, and the optimized reaction conditions were obtained. The optimized Mg3Al–Pro-LDHs catalyst exhibited a much higher MAL selectivity than those of re-MgxAl–LDHs.

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9

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 (February 1, 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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10

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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11

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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12

Rao, Nagaraj. "ASYMMETRIC ORGANOCATALYSIS." INDIAN DRUGS 58, no. 10 (December 16, 2021): 5–6. http://dx.doi.org/10.53879/id.58.10.p0005.

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Dear Reader, Two basic reactions that were taught to us in the organic chemistry courses were the aldol condensation reaction and the Diels-Alder reaction. In aldol condensation, discovered by the French chemist Charles Wurtz in 1872, an enolate ion reacts with a carbonyl compound in the presence of an acid/ base catalyst to form a β-hydroxy aldehyde or a β-hydroxy ketone, usually followed by dehydration to give a conjugated enone. If the enolate ion and the carbonyl group are present in the same molecule, then the aldol reaction is intramolecular. It is an extremely useful carbon-carbon bond-forming reaction. The Diels-Alder reaction, discovered in 1928 by the German chemist Otto Diels and his student Kurt Alder, is the reaction between a conjugated diene and an alkene, a so-called dienophile, to form an unsaturated six-membered ring. It is called a cycloaddition reaction, since the reaction involves the formation of a cyclic product via a cyclic transition state. Uncatalysed Diels– Alder reactions usually require extended reaction times at elevated pressures and temperatures with the formation of by-products, hence various catalysts are employed. The Diels-Alder reaction also has great industrial relevance and the discoverers were crowned with the 1950 Nobel Prize in Chemistry. The aldol condensation reaction and the Diels-Alder reaction typically require catalysts, basically Brønsted acids, Brønsted bases, Lewis acids or Lewis bases. This triggered the minds of Dr. David MacMillan and Dr. Benjamin List for different reasons at different locations in USA around not so different times, more than twenty years ago, culminating in their being jointly awarded the Nobel Prize in Chemistry for this year.

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13

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 (December 19, 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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14

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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15

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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16

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 inclusion of a water molecule bonded to the amino ketones resulted in increased stability of the enol forms. The dependence of the anti/syn-diastereoselectivity on the amount of water used may be rationalized on the basis of change in the polarity of the reaction medium. The predicted stabilities of competing products agreed with experimental results supporting the notion of thermodynamic control. The isomeric products distributions for the aldol reaction of several aromatic aldehydes in solventless (neat) conditions were accurately calculated from free energies of the aldol addition step in the gas phase using B3LYP/6-31g(d) method and in aqueous conditions using the CPCM-B3LYP/6-31g(d) model. Our methodology can be useful for predicting the outcome of this type of aldol reactions.

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17

Eaton, Richard W. "trans-o-Hydroxybenzylidenepyruvate Hydratase-Aldolase as a Biocatalyst." Applied and Environmental Microbiology 66, no. 6 (June 1, 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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18

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 (June 24, 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, 98:2 dr). A low catalyst loading of only 2-5 mol % of the β-tosylamidoprolinamide catalyst was needed to obtain the desired aldol products in good to high yields and high stereoselectivities. Methods: By carefully adjusting the hydrogen bonding ability of the remote β-amide hydrogen of the 1,2-diamine-based prolinamide bifunctional catalysts, the catalytic activity and the asymmetric induction of these catalysts were significantly improved for the direct aldol reaction between aldehydes and enolizable ketones. Conclusion: Some highly efficient 1,2-diamine-based bifunctional prolinamide catalysts have been developed through probing the remote β-amide hydrogen for its hydrogen bonding capability. These catalysts are easy to synthesize and high enantioselectivities may be achieved at very low catalyst loadings.

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19

Dao Cai Wang, Dao Cai Wang, Cong Wu Cong Wu, Chi Zhang Chi Zhang, Fang Zhen Zhou Fang Zhen Zhou, and Hang Song and Xiao Peng Liu Hang Song and Xiao Peng Liu. "Efficient Construction of 4-hydroxy-4-arylbutan-2-ones through an Enantioselective Aldol Reaction Mediated by a Recoverable Proline-Based Chiral Ionic Liquid." Journal of the chemical society of pakistan 42, no. 2 (2020): 243. http://dx.doi.org/10.52568/000629.

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Chiral ionic liquid derived from L-proline worked as an excellent organocatalyst for the enantioselective aldol reaction of aromatic aldehydes and acetone. The reaction was conducted in the presence of [BMIM][BF4] as reaction medium. The substrate scope of aldol reaction was successfully explored for various aromatic aldehydes under the mild conditions. The generated aldol products were separated by column chromatography with moderate to good yields as well as enantioselectivities. The main advantage of this catalytic method was that the catalyst and solvent could be recovered at the same time and reused for at least five times with satisfactory performance.

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20

Dao Cai Wang, Dao Cai Wang, Cong Wu Cong Wu, Chi Zhang Chi Zhang, Fang Zhen Zhou Fang Zhen Zhou, and Hang Song and Xiao Peng Liu Hang Song and Xiao Peng Liu. "Efficient Construction of 4-hydroxy-4-arylbutan-2-ones through an Enantioselective Aldol Reaction Mediated by a Recoverable Proline-Based Chiral Ionic Liquid." Journal of the chemical society of pakistan 42, no. 2 (2020): 243. http://dx.doi.org/10.52568/000629/jcsp/42.02.2020.

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Chiral ionic liquid derived from L-proline worked as an excellent organocatalyst for the enantioselective aldol reaction of aromatic aldehydes and acetone. The reaction was conducted in the presence of [BMIM][BF4] as reaction medium. The substrate scope of aldol reaction was successfully explored for various aromatic aldehydes under the mild conditions. The generated aldol products were separated by column chromatography with moderate to good yields as well as enantioselectivities. The main advantage of this catalytic method was that the catalyst and solvent could be recovered at the same time and reused for at least five times with satisfactory performance.

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21

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

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22

Mondal, Anirban, and Kartick Chandra Bhowmick. "Asymmetric Direct Aldol Reaction Catalyzed by (1R, 2R)-(+)-1, 2- Diammonium Cyclohexane-L-tartrate in Water." Current Organocatalysis 6, no. 2 (June 24, 2019): 165–70. http://dx.doi.org/10.2174/2213337206666181227151140.

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Background: A cheap and commercially available organocatalyst, (1R, 2R)-(+)-1, 2- diammonium cyclohexane-L-tartrate 1 was applied in direct aldol reaction in water. The organocatalyst 1 afforded aldol products from cyclohexanone and substituted aromatic aldehydes with high yield (up to 90%) and good stereoselectivity (up to 99% ee and up to 11.5:1 dr) in large volume of water (10 ml). Methods: The same aldol reaction when carried out in the presence of more expensive organocatalyst e.g. (1R, 2R)-(+)-1,2-diaminocyclohexane and 1,6-hexanediaoic acid as acid additive furnished the aldol products with only 20% yield, 2:1 anti/syn ratio and 92% ee. Results and Conclusion: In summary, we have applied a reasonably cheap and commercially available organocatalyst 1 for highly enantioselective direct aldol reaction in water at room temperature.

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23

Lee, Yoon Joo, and Tak Hang Chan. "Organometallic reactions in aqueous media Bismuth-mediated crossed aldol type reactions." Canadian Journal of Chemistry 81, no. 11 (November 1, 2003): 1406–12. http://dx.doi.org/10.1139/v03-142.

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Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syn-diastereoselective.Key words: bismuth, zinc fluoride, aldol reaction, regioselectivity, aqueous media.

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24

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 structures. As part of this study, the aldol reaction of the starting 2-substituted carbaldehyde with acetone was also performed, which produced the thieno-fused benzobicyclo[3.2.1]octadiene compound with an extended conjugation.

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25

Llanes, Patricia, Sonia Sayalero, Carles Rodríguez-Escrich, and Miquel A. Pericàs. "Asymmetric cross- and self-aldol reactions of aldehydes in water with a polystyrene-supported triazolylproline organocatalyst." Green Chemistry 18, no. 12 (2016): 3507–12. http://dx.doi.org/10.1039/c6gc00792a.

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A PS-immobilized triazolylproline prepared by co-polymerization with full regiocontrol swells in water and catalyzes the enantioselective cross-aldol reaction and the self-aldol reaction of aldehydes under essentially neat conditions with excellent stereocontrol.

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26

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 (October 3, 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 and aldehydes afforded the anticipated aldol products with excellent yields and moderate diastereo- and enantioselectivities. The recommended experimental protocol is simple, fast, and efficient providing the enantioenriched aldol product, usually without the need of a special work-up or purification protocol. This approach constitutes a remarkable improvement in the field of heterogeneous (S)-proline-based organocatalysis; in particular, the solid-phase silica-bonded catalytic systems described herein allow for a substantial reduction in solvent usage. Furthermore, the supported system described here can be recovered, reactivated, and reused several times with limited loss in catalytic efficiency relative to freshly synthesized organocatalysts.

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27

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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28

Caracoti, Andrei, and Robert A. Flowers, II. "SmI2-mediated nitrile aldol reaction." Tetrahedron Letters 41, no. 17 (April 2000): 3039–41. http://dx.doi.org/10.1016/s0040-4039(00)00348-8.

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29

Gati, Wafa, and Hisashi Yamamoto. "Second Generation of Aldol Reaction." Accounts of Chemical Research 49, no. 9 (August 11, 2016): 1757–68. http://dx.doi.org/10.1021/acs.accounts.6b00243.

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30

Flanagan, Mark E., John R. Jacobsen, Elizabeth Sweet, and Peter G. Schultz. "Antibody-Catalyzed Retro-Aldol Reaction." Journal of the American Chemical Society 118, no. 25 (January 1996): 6078–79. http://dx.doi.org/10.1021/ja954221u.

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31

Izumiseki, Atsuto, and Hisashi Yamamoto. "Intermolecular/Intramolecular Sequential Aldol Reaction." Journal of the American Chemical Society 136, no. 4 (January 21, 2014): 1308–11. http://dx.doi.org/10.1021/ja413008a.

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32

Mlynarski, Jacek. "Direct Asymmetric Aldol-Tishchenko Reaction." European Journal of Organic Chemistry 2006, no. 21 (November 2006): 4779–86. http://dx.doi.org/10.1002/ejoc.200600258.

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33

Machajewski, Timothy D., and Chi-Huey Wong. "The Catalytic Asymmetric Aldol Reaction." Angewandte Chemie International Edition 39, no. 8 (April 17, 2000): 1352–75. http://dx.doi.org/10.1002/(sici)1521-3773(20000417)39:8<1352::aid-anie1352>3.0.co;2-j.

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34

Yliniemela-Sipari, S. M., and P. M. Pihko. "ChemInform Abstract: Direct Aldol Reaction." ChemInform 42, no. 40 (September 8, 2011): no. http://dx.doi.org/10.1002/chin.201140204.

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35

Shibasaki, Masakatsu, and Harald Groger. "ChemInform Abstract: Nitro Aldol Reaction." ChemInform 31, no. 18 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200018228.

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36

Carreira, Erick M. "ChemInform Abstract: Mukaiyama Aldol Reaction." ChemInform 31, no. 18 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200018230.

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37

Mandal, Swagata, Sangita Mandal, Sumanta K. Ghosh, Aniruddha Ghosh, Rumpa Saha, Soujanya Banerjee, and Bidyut Saha. "Review of the aldol reaction." Synthetic Communications 46, no. 16 (August 13, 2016): 1327–42. http://dx.doi.org/10.1080/00397911.2016.1206938.

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38

Riant, O., O. Chuzel, J. Deschamps, and C. Chausteur. "Stereoselective Tandem Reductive Aldol Reaction." Synfacts 2007, no. 3 (March 2007): 0313. http://dx.doi.org/10.1055/s-2007-968183.

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Nishiyama, H., and T. Shiomi. "Intermolecular Asymmetric Reductive Aldol Reaction." Synfacts 2007, no. 7 (July 2007): 0730. http://dx.doi.org/10.1055/s-2007-968663.

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40

Howarth, Judith A., W. Martin Owton, and Jonathan M. Percy. "The aldol reaction with difluoroenolates." Journal of the Chemical Society, Chemical Communications, no. 7 (1995): 757. http://dx.doi.org/10.1039/c39950000757.

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41

Li, Guigen, Xin Xu, Dianjun Chen, Cody Timmons, Michael D. Carducci, and Allan D. Headley. "Asymmetric Halo Aldol Reaction (AHA)." Organic Letters 5, no. 3 (February 2003): 329–31. http://dx.doi.org/10.1021/ol027344+.

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42

Yoshikawa, Naoki, Yoichi M. A. Yamada, Jagattaran Das, Hiroaki Sasai, and Masakatsu Shibasaki. "Direct Catalytic Asymmetric Aldol Reaction." Journal of the American Chemical Society 121, no. 17 (May 1999): 4168–78. http://dx.doi.org/10.1021/ja990031y.

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43

Kalesse, Markus, Dirk Landsberg, Olaf Hartmann, and Ulrike Eggert. "Diastereodivergent Vinylogous Mukaiyama Aldol Reaction." Synlett 24, no. 09 (April 29, 2013): 1105–8. http://dx.doi.org/10.1055/s-0033-1338933.

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44

Li, Hai-Hong, Yan-Hong He, and Zhi Guan. "Protease-catalyzed direct aldol reaction." Catalysis Communications 12, no. 7 (March 2011): 580–82. http://dx.doi.org/10.1016/j.catcom.2010.12.003.

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45

Szlosek, Magali, and Bruno Figadère. "Highly Enantioselective Aldol Reaction with 2-Trimethylsilyloxyfuran: The First Catalytic Asymmetric Autoinductive Aldol Reaction." Angewandte Chemie International Edition 39, no. 10 (May 15, 2000): 1799–801. http://dx.doi.org/10.1002/(sici)1521-3773(20000515)39:10<1799::aid-anie1799>3.0.co;2-z.

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46

Szlosek, Magali, and Bruno Figadère. "Highly Enantioselective Aldol Reaction with 2-Trimethylsilyloxyfuran: The First Catalytic Asymmetric Autoinductive Aldol Reaction." Angewandte Chemie 112, no. 10 (May 15, 2000): 1869–71. http://dx.doi.org/10.1002/(sici)1521-3757(20000515)112:10<1869::aid-ange1869>3.0.co;2-0.

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47

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 (December 20, 2017): 560–65. http://dx.doi.org/10.1055/s-0036-1591854.

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Abstract:

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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Kawanishi, Ryouta, Shinya Hattori, Seiji Iwasa, and Kazutaka Shibatomi. "Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates." Molecules 24, no. 15 (July 30, 2019): 2773. http://dx.doi.org/10.3390/molecules24152773.

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Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C–C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and trifluoropyruvates proceeded smoothly to yield the corresponding aldol products in high yields and with high diastereoselectivity in the presence of a tertiary amine catalyst. In this reaction, we efficiently constructed a quaternary carbon center and an adjacent trifluoromethylated carbon center. This protocol was also extended to an enantioselective reaction with a chiral amine catalyst, and the desired product was obtained with up to 73% enantioselectivity.

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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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Abstract:

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 presence of water was determined asexo,synby comparison of NMR data of the aldol isomers, in particular vicinal coupling constants and shifts corresponding to the side-chain CH group, with data of related TBDMS derivatives and confirmed by single-crystal X-ray diffraction.

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Kamimura, Akio, Hiromasa Mitsudera, Yoji Omata, Kenji Matsuura, Masashi Shirai, and Akikazu Kakehi. "Magnesium cation-induced anti-aldol selective tandem Michael/aldol reaction." Tetrahedron 58, no. 49 (December 2002): 9817–26. http://dx.doi.org/10.1016/s0040-4020(02)01299-1.

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