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Relevant bibliographies by topics / Intramolecular aldol reaction

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Academic literature on the topic 'Intramolecular aldol reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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Journal articles on the topic "Intramolecular aldol reaction"

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

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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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Satpathi, Bishnupada, Lona Dutta, and S. S. V. Ramasastry. "Phosphine- and water-promoted pentannulative aldol reaction." Organic & Biomolecular Chemistry 17, no. 6 (2019): 1547–51. http://dx.doi.org/10.1039/c8ob03106a.

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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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Banachowicz, Piotr, and Szymon Buda. "Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction." RSC Advances 9, no. 23 (2019): 12928–35. http://dx.doi.org/10.1039/c9ra02002k.

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Izumiseki, Atsuto, and Hisashi Yamamoto. "ChemInform Abstract: Intermolecular/Intramolecular Sequential Aldol Reaction." ChemInform 45, no. 35 (2014): no. http://dx.doi.org/10.1002/chin.201435191.

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Kawamoto, Yuichiro, Daiki Ozone, Toyoharu Kobayashi, and Hisanaka Ito. "Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction." Organic & Biomolecular Chemistry 16, no. 44 (2018): 8477–80. http://dx.doi.org/10.1039/c8ob02557f.

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Stepanova, Ekaterina, Andrey Maslivets, Svetlana Kasatkina, and Maksim Dmitriev. "Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones." Synthesis 50, no. 24 (2018): 4897–904. http://dx.doi.org/10.1055/s-0037-1610647.

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A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intra

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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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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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Dissertations / Theses on the topic "Intramolecular aldol reaction"

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Freiria, Marta. "Novel rhodium (I) catalysed tandem hydrosilylation - intramolecular aldol reaction." Thesis, University College London (University of London), 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.409927.

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Atkinson, Duncan. "Novel methods for allylic amination by an intramolecular nitroso ene reaction." Thesis, Loughborough University, 2013. https://dspace.lboro.ac.uk/2134/14069.

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C-H functionalisation reactions aim for the selective cleavage of C-H bonds, and formation of a new carbon or heteroatom bond, often with the use of a transition metal catalyst. These reactions offer potential for functionalisation of hydrocarbons in fewer steps than conventional methods, and with high atom efficiency. They are therefore a subject of intense research in organic synthesis. Carbon-heteroatom bond forming reactions are particularly sought after, and useful in the efficient synthesis of many biologically significant groups such as oxazolidinone rings, 1,2 or 1,3 amino alcohols and

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Abramite, Joseph A. "The intramolecular Yamamoto vinylogous aldol reaction and its application in the total synthesis of (+)-peloruside A." Connect to online resource, 2008. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqdiss&rft_dat=xri:pqdiss:3337042.

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司徒振邦 and Chun-pong Szeto. "Studies on the use of (triphenylphosphine)copper(I) hydride hexamer inthe tandem reduction-intramolecular aldol cyclisation reaction." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2000. http://hub.hku.hk/bib/B31223412.

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Szeto, Chun-pong. "Studies on the use of (triphenylphosphine)copper(I) hydride hexamer in the tandem reduction-intramolecular aldol cyclisation reaction /." Hong Kong : University of Hong Kong, 2000. http://sunzi.lib.hku.hk/hkuto/record.jsp?B21827369.

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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 react

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Richards, Elinor Louise. "Tandem Michael/intramolecular aldo reactions mediated by secondary amines, thiols and phosphines." Thesis, Bangor University, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.273662.

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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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Wang, Li-Hsiang, and 王立翔. "Rhodium(I)/ Chiral Diene-Catalyzed Regioselective Ring Opening of Benzocyclobutenols and Subsequent Enantioselective Insertion and Intramolecular Aldol Reaction with Diazoesters." Thesis, 2017. http://ndltd.ncl.edu.tw/handle/56ssnd.

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碩士<br>國立臺灣師範大學<br>化學系<br>105<br>In this thesis, a Rh(I)-catalyzed regioselective ring cleavage of benzocyclobutenols 7 followed by enantioselective rhodium carbene insertion with various diazoesters 8 , and subsequent intramolecular aldol reaction via the thus obtained rhodium enolates is described. This transformation proceeds at 60 °C, in the presence 5 mol% of Rh(I) / L1C catalyst, to offer the corresponding products possessing two contiguous quaternary stereo-centers with up to 82% yield, and 95% ee.

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Chamni, Supakarn. "New Diazo Reagents and Applications of β-Lactones for Synthesis and Biological Evaluation of Natural Products". Thesis, 2011. http://hdl.handle.net/1969.1/ETD-TAMU-2011-12-10413.

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Natural products are essential tools for basic cellular studies leading to the identification of medically relevant protein targets and the discovery of potential therapeutic agents. We have developed a set of second generation diazo reagents with small steric footprints, namely an alpha-trifluoroethyl (HTFB) diazo reagent, for simultaneous arming and SAR studies of bioactive natural products. The Rh(II)-catalyzed O-H insertions of several alcohol-containing natural products, including the potent translation inhibitor lactimidomycin, are investigated and useful reactivity and both chemo- and s

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Book chapters on the topic "Intramolecular aldol reaction"

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Singh, R. P., and L. Deng. "Intramolecular Aldol Reaction of Diketones." In Brønsted Base and Acid Catalysts, and Additional Topics. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00079.

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Terada, M., and N. Momiyama. "Intramolecular Aldol Reaction (Robinson-Type Annulation)." In Brønsted Base and Acid Catalysts, and Additional Topics. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00157.

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Marsden, S. P. "Tandem Michael Addition/Intramolecular Aldol Reaction (Robinson Annulation)." In Ketones. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-026-01026.

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4

Taber, Douglass F. "Alkaloid Synthesis: (+)-Deoxoprosopinine (Krishna), Alkaloid (–)-205B (Micalizio), FR901483 (Huang), (+)-Ibophyllidine (Kwon), (–)-Lycoposerramine-S (Fukuyama), (±)-Crinine (Lautens)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0060.

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Palakodety Radha Krishna of the Indian Institute of Chemical Technology observed (Synlett 2012, 2814) high stereocontrol in the addition of allyltrimethylsilane to the cyclic imine derived from 1. The product piperidine 2 was carried onto (+)-deoxoprosopinine 3. Glenn C. Micalizio of Scripps Florida condensed (J. Am. Chem. Soc. 2012, 134, 15237) the amine 4 with 5. The ensuing intramolecular dipolar cycloaddition led to 6, which was carried onto the Dendrobates alkaloid (–)-205B 7. Pei-Qiang Huang of Xiamen University showed (Org. Lett. 2012, 14, 4834) that the quaternary center of 9 could be established with high diastereoselectivity by activation of the lactam 8, then sequential addition of two different Grignard reagents. Subsequent stereoselective intramolecular aldol condensation led to FR901843 10. More recently, Professor Huang, with Hong-Kui Zhang, also of Xiamen University, published (J. Org. Chem. 2013, 78, 455) a full account of this work. In an elegant application of the power of phosphine-catalyzed intermolecular allene cycloaddition, Ohyun Kwon of UCLA added (Chem. Sci. 2012, 3, 2510) 12 to the imine 11 to give 13. The cyclization elegantly set two of the four stereogenic centers of (+)-ibophyllidine 14. Tohru Fukuyama of the University of Tokyo initiated (Angew. Chem. Int. Ed. 2012, 51, 11824) a cascade cyclization between the enone 15 and the chiral auxiliary 16. The product lactam 17 was carried onto (–)-lycoposerramine-S 18. Mark Lautens explored (J. Am. Chem. Soc. 2012, 134, 15572) the utility of the intramolecular aryne ene reaction, as illustrated by the cyclization of 19 to 20. Oxidation cleavage of the vinyl group of 20 followed by an intramolecular carbonyl ene reaction led to (±)-crinine 21.

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Pápai, I. "Intramolecular Aldol Reactions." In Brønsted Base and Acid Catalysts, and Additional Topics. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00450.

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MacMillan, D. W. C., and A. J. B. Watson. "Intramolecular Aldol Reactions." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00429.

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Scott, P. J. H., and P. G. Steel. "Intramolecular Aldol Reactions." In Alcohols. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00417.

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8

Nelson, A. "Intramolecular Aldol Reactions." In Six-Membered Hetarenes with One Chalcogen. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-014-00971.

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Taber, Douglass. "The Carter Synthesis of (-)-Lycopodine." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0099.

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Rich G. Carter of Oregon State University described (J. Am. Chem. Soc. 2008, 130, 9238) the first enantioselective synthesis of the Lycopodium alkaloid (-)-lyopodine 3. A key step in the assembly of 3 was the diastereoselective intramolecular Michael addition of the keto sulfone of 1 to the enone, leading to the cyclohexanone 2. The key cyclization substrate 1 bore a single secondary methyl group. While that could have been derived from a natural product, it was operationally easier to effect chiral auxiliary controlled conjugate addition to the crotonyl amide 4, leading, after methoxide exchange, to the ester 5. The authors reported that double deprotonation with LiTMP gave superior results, vs. LDA or BuLi, in the condensation of 6 with 5 to give 7. Metathesis with pentenone 8 gave the intramolecular Michael substrate 1. The authors thought that they would need a chiral catalyst to drive the desired stereocontrol in the cyclization of 1 to 2. As a control, they tried an achiral base first, and were pleased to observe the desired diastereomer crystallize from the reaction mixture in 89% yield. The structure of 2 was confirmed by X-ray crystallography. To prepare for the intramolecular Mannich condensation, the azide was reduced to give the imine, and the methyl ketone was converted to the silyl enol ether. Under Lewis acid conditions, the sulfonyl group underwent an unanticipated 1,3-migration, to give 11. Cyclization of 12 then delivered the crystalline 14. Reduction converted 14 to the known (in racemic form) ketone 15. To complete the synthesis, the amine 15 was alkylated with 16 to give the alcohol 17. Oppenauer oxidation followed by aldol condensation delivered the cyclized enone, that was reduced with the Stryker reagent to give (-)-Lycopodine 3. Both the cyclization of 1 to 2 and the cyclization of 9 to 14 are striking. It may be that the steric demand of the phenylsulfonyl group destabilizes the competing transition state for the cyclization of 1.

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Taber, Douglass F. "Carbocyclic Ring Construction: The Nicolaou Synthesis of Myceliothermophin E." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0082.

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Nan Zheng of the University of Arkansas developed (Adv. Synth. Catal. 2014, 356, 2831) a Ru catalyst for the addition of an amino cyclopropane 1 to an alkyne 2 to give 3. The reaction proceeded with high regiocontrol, but only modest stereocontrol. Alain De Mesmaeker of Syngenta Crop Protection, Switzerland found (Tetrahedron Lett. 2014, 55, 6577) that the β,γ-unsaturated amide 4 worked particularly well as a precursor to the keteniminium that cyclized to give, after hydrolysis, the cyclobutanone 5. Baeyer–Villiger oxidation of 5 led to 5-deoxystrigol 6. David Tymann and Martin Hiersemann of the Technische Universität Dortmund have been exploring (Org. Lett. 2014, 16, 4062; Synthesis 2014, 46, 3110) the intramolecular carbonyl ene reaction as a tool for the assembly of highly substituted cyclopentanes, as in the conversion of 7 to 8. On oxidation, 8 was readily carried on to the alkene 9. James L. Leighton of Columbia University conceived (J. Am. Chem. Soc. 2014, 136, 9878) the cascade transformation of 10 to 12. Deprotonation/silylation set the stage for Claisen rearrangement to give 11. The subsequent Cope rearrangement is an equilibrium process, driven by the ring strain of 11. K. C. Nicolaou of Rice University described (Angew. Chem. Int. Ed. 2014, 53, 10970) the total synthesis of the cytotoxic tetramic acid derivative myceliothermophin E 15. A key step in the synthesis was the intramolecular Michael addition/ aldol condensation that converted 13 to 14.

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