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Relevant bibliographies by topics / Catalytic asymmetric Diels-Alder reaction

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Academic literature on the topic 'Catalytic asymmetric Diels-Alder reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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Journal articles on the topic "Catalytic asymmetric Diels-Alder reaction"

1

Cai, Quan, Xu-Ge Si, and Zhi-Mao Zhang. "Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis." Synlett 32, no. 10 (2021): 947–54. http://dx.doi.org/10.1055/a-1371-4391.

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AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Ac

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Heller, Douglas P., Daniel R. Goldberg, Hongqiao Wu, and William D. Wulff. "An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions." Canadian Journal of Chemistry 84, no. 10 (2006): 1487–503. http://dx.doi.org/10.1139/v06-124.

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Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-d

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Kagan, Henri B., and Olivier Riant. "Catalytic asymmetric Diels Alder reactions." Chemical Reviews 92, no. 5 (1992): 1007–19. http://dx.doi.org/10.1021/cr00013a013.

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Kong, Liman, Xiaoyu Han, and Peng Jiao. "Catalytic asymmetric Diels–Alder reactions involving aryl vinyl ketones." Chem. Commun. 50, no. 91 (2014): 14113–16. http://dx.doi.org/10.1039/c4cc06837h.

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Bădoiu, Andrei, Yasmin Brinkmann, Florian Viton, and E. Peter Kündig. "Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions." Pure and Applied Chemistry 80, no. 5 (2008): 1013–18. http://dx.doi.org/10.1351/pac200880051013.

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Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.

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Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Catalytic Asymmetric Aza-Diels–Alder Reactions: The Povarov Cycloaddition Reaction." Synthesis 46, no. 02 (2013): 135–57. http://dx.doi.org/10.1055/s-0033-1338581.

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Lautens, Mark, Julia Craig Lautens, and A. Catherine Smith. "Catalytic asymmetric induction in the homo Diels-Alder reaction." Journal of the American Chemical Society 112, no. 14 (1990): 5627–28. http://dx.doi.org/10.1021/ja00170a030.

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Yamamoto, Yuhei, and Hisashi Yamamoto. "Catalytic Asymmetric Nitroso-Diels-Alder Reaction with Acyclic Dienes." Angewandte Chemie International Edition 44, no. 43 (2005): 7082–85. http://dx.doi.org/10.1002/anie.200501345.

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Yamamoto, Yuhei, and Hisashi Yamamoto. "Catalytic Asymmetric Nitroso-Diels-Alder Reaction with Acyclic Dienes." Angewandte Chemie 117, no. 43 (2005): 7244–47. http://dx.doi.org/10.1002/ange.200501345.

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Nakano, Hiroto, Yuichiro Suzuki, Chizuko Kabuto, Reiko Fujita, and Hiroshi Hongo. "Chiral Phosphinooxathiane Ligands for Catalytic Asymmetric Diels−Alder Reaction." Journal of Organic Chemistry 67, no. 14 (2002): 5011–14. http://dx.doi.org/10.1021/jo0201474.

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Dissertations / Theses on the topic "Catalytic asymmetric Diels-Alder reaction"

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Yamamoto, Yuhei. "Catalytic asymmetric nitroso Diels-Alder reaction." 京都大学 (Kyoto University), 2006. http://hdl.handle.net/2433/143962.

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Keskin, Eda. "Synthesis Of Heterocyclic Amine Substituted Novel 1,4-aminoalcohols And Applications In Various Asymmetric Transformations." Master's thesis, METU, 2007. http://etd.lib.metu.edu.tr/upload/12608317/index.pdf.

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Aminoalcohols are very important compounds used in various asymmetric transformations as chiral ligands or chiral auxiliaries. In this thesis, four novel heterocyclic amine substituted chiral 1,4-aminoalcohols were synthesized. In the synthetic strategy, amide esters were synthesized from (2S, 3R)-3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid by DCC coupling method. Subsequent reduction of these amide esters lead to target 1,4-aminoalcohols. The activities of these novel chiral 1,4-aminoalcohols were tested in enantioselective diethylzinc addition, Mukaiyama aldol and Diels-Ald

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3

Modin, Stefan. "Developments in the Field of Aza-Diels-Alder Reactions, Catalytic Michael Additions and Automated Synthesis." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, Univ.bibl. [distributör], 2004. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-4640.

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Csatary, Erika Elizabeth. "Asymmetric Multicomponent Aza-Diels-Alder Reaction for Construction of Multicyclic Heterocycles and Development of XZH-5 Derivatives as Inhibitors of Signal Transducer and Activator of Transcription 3 (STAT3)." Miami University / OhioLINK, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=miami1435110305.

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Trifonova, Anna. "Synthesis of Novel Chiral Bicyclic Ligands and their Application in Iridium-Catalyzed Reactions." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, 2005. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-5783.

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Liang, Tao. "Chiral Phosphoric Acids and Alkaline Earth Metal Phosphates Chemistry." Thesis, University of South Florida, 2014. http://pqdtopen.proquest.com/#viewpdf?dispub=3632228.

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<p> Asymmetric synthesis and catalysis is one of the leading research areas in chemistry society, for its versatility and efficiency in obtaining chiral molecules that found the vast majority in natural active compounds and synthetic drugs. Developing asymmetric catalytic methodology is at the frontier in both industrial and academic research laboratories. Enantioselective organocatalysis has emerged as a powerful synthetic tool that is complementary to metal-catalyzed transformations. The development of chiral phosphoric acid and metal phosphate as catalysts has been a breakthrough in recent

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Mellberg, Annika. "Chiral Carbocations as Lewis Acid Catalysts in Diels-Alder Reactions." Thesis, KTH, Skolan för kemivetenskap (CHE), 2012. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-156209.

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Lewis acids can be used as catalysts in different reactions, but the term Lewis acid catalysts often refers to metal salts. Metal complexes have been widely used for asymmetric catalysis. Asymmetric synthesis can however be performed in a metal-free way by using organocatalysis. New Lewis acid catalysts that are more effective, enantioselective and environmental friendly is of interest. This new type of Lewis acid catalysts could for example be of carbocation based character. The aim of this project was to synthesize chiral carbocations with different degree of sterical hindrance and investiga

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Yuyitung, Gay M. "Studies towards a catalytic antibody for an intramolecular Diels-Alder reaction." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1999. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape7/PQDD_0007/NQ39011.pdf.

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Durrant, Steven. "Electronic effects in the Diels-Alder reaction : towards catalytic chiral auxiliaries." Thesis, University of Bath, 2002. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.393873.

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Buckle, Ronald Neil. "Asymmetric Diels-Alder studies involving chiral acetylenic diesters and investigations of an intramolecular Diels-Alder approach to the pentalenolactones." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1998. http://www.collectionscanada.ca/obj/s4/f2/dsk2/ftp03/NQ36199.pdf.

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Books on the topic "Catalytic asymmetric Diels-Alder reaction"

1

Powers, Timothy S. Asymmetric Diels-Alder and aldol reactions using Fischer carbene complexes. 1993.

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Book chapters on the topic "Catalytic asymmetric Diels-Alder reaction"

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Evans, David A., and Jeffrey S. Johnson. "Diels-Alder Reactions." In Comprehensive Asymmetric Catalysis I–III. Springer Berlin Heidelberg, 1999. http://dx.doi.org/10.1007/978-3-642-58571-5_8.

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Ooi, Takashi, and Keiji Maruoka. "Hetero-Diels-Alder and Related Reactions." In Comprehensive Asymmetric Catalysis I–III. Springer Berlin Heidelberg, 1999. http://dx.doi.org/10.1007/978-3-642-58571-5_9.

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Mikami, K., Y. Matsumoto, and T. Shiono. "Catalytic Asymmetric Diels–Alder and Hetero-Diels–Alder Reactions." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...). Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-002-00769.

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4

Nagasawa, K., and Y. Sohtome. "Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reactions." In Brønsted Base and Acid Catalysts, and Additional Topics. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00030.

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Vedantham, P., M. Jiménez, and P. R. Hanson. "Asymmetric Diels–Alder Reaction." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00217.

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Urgaonkar, S., and J. G. Verkade. "Asymmetric Diels–Alder Reaction." In Organophosphorus Compounds (incl. RO-P and RN-P). Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-042-01119.

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Wada, Eiji, Hidetaka Koga, and Tomoyuki Manabe. "A New Methodology of Catalytic Asymmetric Intramolecular Hetero Diels-Alder Reaction for Construction of Fused Heterocycles with Methyl (E)-4-Methoxy-2-oxo-3-butenoate." In 19th International Congress on Heterocyclic Chemistry. Elsevier, 2003. http://dx.doi.org/10.1016/b978-0-08-044304-1.50348-8.

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Lambert, Tristan H. "Total Synthesis of C–O Ring-Containing Natural Products." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0053.

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Scott A. Snyder at Columbia University demonstrated (J. Am. Chem. Soc. 2012, 134, 17714) that tetrahydrofuran 1 could be readily converted to oxocane 2 by treatment with the BDSB reagent developed in his laboratory. Reduction of 2 with DIBAL-H initiated a second ring closure by mesylate displacement to form the bicycle 3, which represented a formal total synthesis of laurefucin 4. Andrew L. Lawrence at the Australian National University found (Org. Lett. 2012, 14, 4537) that upon treatment with catalytic base, rengyolone 6, which was prepared in one pot from phenol 5, could be converted to the natural products incarviditone 7 and incarvilleatone 8. This demonstration provides strong support for the postulated biomimetic formation of these natural products. Shuanhu Gao at East China Normal University reported (Angew. Chem. Int. Ed. 2012, 51, 7786) the total synthesis of (+)-fusarisetin A 12 via biomimetic oxidation of equisetin 10 to produce the peroxy compound 11, followed by reduction. The bicyclic carbon skeleton of equisetin 10 was synthesized by intramolecular Diels-Alder reaction of trienyl aldehyde 9. The ellagitannin natural product (+)-davidiin 15 possesses a glucopyranose core with the unusual 1C4 (tetraaxial) conformation due to the presence of a biaryl bridge between two of the galloyl groups. Hidetoshi Yamada at Kwansei Gakuin University constructed (Angew. Chem. Int. Ed. 2012, 51, 8026) this bridge by oxidation with CuCl2 of 13, in which the three sterically demanding triisopropylsiloxy groups enforce the requisite tetraaxial conformation. John A. Porco, Jr. at Boston University applied (J. Am. Chem. Soc. 2012, 134, 13108) his asymmetric [3+2] photocycloaddition chemistry to the total synthesis of the aglain natural product (+)-ponapensin 20. Irradiation of hydroxyflavone 16 with methyl cinnamate 17 in the presence of diol 18 afforded the entire core framework 19 of ponapensin 20, which was accessed in just a few further synthetic transformations. Finally, Silas P. Cook at Indiana University reported (J. Am. Chem. Soc. 2012, 134,13577) a five-pot total synthesis of the antimalarial (+)-artemisinin 25. Cyclohexenone 21 was converted by simple operations to aldehyde 22. This aldehyde was then engaged in a [4+2] cycloaddition with the silyl ketene acetal 23 to produce, after an impressive Wacker oxidation of the disubstituted olefin, bicycle 24.

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Garbaccio, R. M., and S. E. Wolkenberg. "Catalytic Asymmetric Diels–Alder Addition to Chiral Imino Esters." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-01097.

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Lambert, Tristan H. "Construction of Stereochemical Arrays." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0045.

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The unprecedented enantioselective 1,8-addition of azlactone 1 to acylpyrrole 2 catalyzed by triaminophosphorane 3 was reported (J. Am. Chem. Soc. 2012, 134, 19370) by Takashi Ooi at Nagoya University. Tomislav Rovis at Colorado State University developed (Angew. Chem. Int. Ed. 2012, 51, 12330) the asymmetric oxidative hetero-Diels-Alder reaction of propionaldehyde (5) and ketone 6 to produce lactone 8, catalyzed by NHC catalyst 7 in the presence of phenazine. A related NHC catalyst 11 was utilized (Angew. Chem. Int. Ed. 2012, 51, 8276) by Xue-Wei Liu at Nanyang Technological University for the homoenolate addition of enal 9 to nitrodiene 10 to furnish 12 with high ee. The vinylogous conjugate addition of butenolide 13 to 15 to produce 16 with exquisite stereoselectivity was accomplished (Angew. Chem. Int. Ed. 2012, 51, 10069) by Kuo-Wei Huang at KAUST, Choon-Hong Tan at Henan University and Nanyang Technological University, and Zhiyong Jiang at Henan University. The enantioselective production of lactone 18 was achieved (J. Am. Chem. Soc. 2012, 134, 20197) by Jeffrey S. Johnson at the University of North Carolina at Chapel Hill by dynamic kinetic resolution (DKR) of α-keto ester 17. A related DKR strategy was employed (Org. Lett. 2012, 14, 6334) by Brinton Seashore-Ludlow at the KTH Royal Institute of Technology and Peter Somfai at Lund University in Sweden and the University of Tartu in Estonia for hydrogenation of α-amino-β-ketoester 19 to furnish aminoalcohol 21 with high Shigeki Matsunaga and Motomu Kanai at the University of Tokyo developed (Angew. Chem. Int. Ed. 2012, 51, 10275) a unique strategy for the selective production of the cross-aldol adduct 24 by in situ generation of an aldehyde enolate from allyloxyborane 23 under rhodium catalysis. The highly diastereoselective construction of adduct 26 bearing two adjacent quaternary stereocenters by ketone allylation with allyl sulfide 25 was reported (Angew. Chem. Int. Ed. 2012, 51, 7263) by Takeshi Takeda at the Tokyo University of Agriculture and Technology. Wen-Hao Hu at East China Normal University reported (Nature Chem. 2012, 4, 733) the enantioselective three-component coupling of diazoester 27, N-benzylindole (28), and imine 29 to furnish 31 under the action of Rh2(OAc)4 and phosphoric acid 30.

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Conference papers on the topic "Catalytic asymmetric Diels-Alder reaction"

1

Vo-Thanh, Giang, Bruce Pégot, Olivier Van Buu, and Didier Gori. "Asymmetric aza-Diels-Alder reaction of Danishefsky’s diene with imines in a chiral reaction medium." In The 10th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2006. http://dx.doi.org/10.3390/ecsoc-10-01378.

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