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Journal articles on the topic 'Diels-Alder reaction. Chirality'

Author: Grafiati
Published: 4 June 2021
Last updated: 12 February 2022

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1

Zwanenburg, Binne, Andries A. Volkers, and Antonius J. H. Klunder. "Use of Flash Vacuum Thermolysis in a Stereocontrolled Synthesis of Optically Active Alkyl-substituted Cyclopentenones with Fragrant Properties." Australian Journal of Chemistry 67, no. 9 (2014): 1234. http://dx.doi.org/10.1071/ch14093.

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The synthesis of four pairs of enantiopure antipodal substituted cyclopentenones is described. The synthetic sequences first comprise the preparation of a tricyclo[5.2.1.02,6]deca-4,8-dienone system, a subsequent kinetic enzymatic resolution of the appropriately functionalized tricyclic system, followed by a series of chemical transformations to install the desired substituents, and finally a retro Diels–Alder reaction using flash vacuum thermolysis to give the target products in high chemical and optical yields. The strategy makes effective use of the concept of transient chirality involving
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2

Uemura, Naohiro, Seiya Toyoda, Waku Shimizu, Yasushi Yoshida, Takashi Mino, and Masami Sakamoto. "Absolute Asymmetric Synthesis Involving Chiral Symmetry Breaking in Diels–Alder Reaction." Symmetry 12, no. 6 (2020): 910. http://dx.doi.org/10.3390/sym12060910.

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Efficient generation and amplification of chirality from prochiral substrates in the Diels–Alder reaction (DA reaction) followed by dynamic crystallization were achieved without using an external chiral source. Since the DA reaction of 2-methylfuran and various maleimides proceeds reversibly, an exo-adduct was obtained as the main product as the reaction proceeded. From single crystal X-ray structure analysis, it was found that five of ten exo-adducts gave conglomerates. When 2-methylfuran and various maleimides with a catalytic amount of TFA were reacted in a sealed tube, the exo-DA adducts w
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3

Pineschi, Mauro, Federica Del Moro, Paolo Crotti, and Franco Macchia. "Catalytic asymmetric ring-opening of cyclopentadiene - heterodienophile cycloadducts with organometallic reagents." Pure and Applied Chemistry 78, no. 2 (2006): 463–67. http://dx.doi.org/10.1351/pac200678020463.

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An unprecedented catalytic asymmetric ring-opening of easily accessible 2,3-heterosubstituted norbornenes with hard alkyl metals (R-M), is able to give a practical regio- and stereoselective access to hetero-functionalized alkyl cyclopentenes in an enantioenriched form. The copper-catalyzed desymmetrization reaction with trialkylaluminums of sterically hindered and rigid, tri- or tetracyclic Diels-Alder adducts, easily available by cycloaddition reaction of cyclopentadiene with 4-phenyl-urazole and 2,3-phthalazine-1,4-dione, proved to be particularly efficient. Interestingly, the chirality of
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4

Shibata, Takanori, Ayato Sekine, Akihito Mitake, and Kyalo Stephen Kanyiva. "Intramolecular Consecutive Dehydro-Diels-Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality." Angewandte Chemie 130, no. 48 (2018): 16088–91. http://dx.doi.org/10.1002/ange.201810174.

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5

Shibata, Takanori, Ayato Sekine, Akihito Mitake, and Kyalo Stephen Kanyiva. "Intramolecular Consecutive Dehydro-Diels-Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality." Angewandte Chemie International Edition 57, no. 48 (2018): 15862–65. http://dx.doi.org/10.1002/anie.201810174.

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6

Chen, Jingjin, Andrew J. Ferreira, and Christopher M. Beaudry. "Synthesis of Bis(indole) Alkaloids fromArundo donax:The Ynindole Diels-Alder Reaction, Conformational Chirality, and Absolute Stereochemistry." Angewandte Chemie 126, no. 44 (2014): 12125–28. http://dx.doi.org/10.1002/ange.201407336.

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7

Chen, Jingjin, Andrew J. Ferreira, and Christopher M. Beaudry. "Synthesis of Bis(indole) Alkaloids fromArundo donax:The Ynindole Diels-Alder Reaction, Conformational Chirality, and Absolute Stereochemistry." Angewandte Chemie International Edition 53, no. 44 (2014): 11931–34. http://dx.doi.org/10.1002/anie.201407336.

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8

Chen, Jingjin, Andrew J. Ferreira, and Christopher M. Beaudry. "ChemInform Abstract: Synthesis of Bis(indole) Alkaloids from Arundo donax: The Ynindole Diels-Alder Reaction, Conformational Chirality, and Absolute Stereochemistry." ChemInform 46, no. 14 (2015): no. http://dx.doi.org/10.1002/chin.201514029.

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9

Togni, Antonio, and Stephen D. Pastor. "Cooperativity of chirality in homogeneous catalysis: The gold(I)-catalyzed aldol reaction and the vanadium(IV)-catalyzed hetero Diels-Alder cycloaddition." Chirality 3, no. 4 (1991): 331–40. http://dx.doi.org/10.1002/chir.530030419.

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10

TOGNI, A., and S. D. PASTOR. "ChemInform Abstract: Cooperativity of Chirality in Homogeneous Catalysis: The Gold(I)- Catalyzed Aldol Reaction and the Vanadium(IV)-Catalyzed Hetero-Diels- Alder Cycloaddition." ChemInform 23, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199211297.

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11

Elbert, Sven M., Kevin Baumgärtner, Joshua A. Esteves, Laura Weber, Frank Rominger, and Michael Mastalerz. "Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes." Organic Materials 02, no. 04 (2020): 358–61. http://dx.doi.org/10.1055/s-0040-1721851.

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Two bench-stable and readily accessible pyrene-based diaryne precursors based on triflate as well as TMS triflate motifs are introduced and compared in their [4+2]-Diels–Alder reactions with tetracyclone to give an oligophenyl-substituted dibenzo[e,l]pyrene in both cases. By single-crystal X-ray analysis, this twistacene showed helical chirality and an end-to-end contortion of 49.6° due to steric repulsion.
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12

Scott, Lawrence T. "Methods for the chemical synthesis of carbon nanotubes: an approach based on hemispherical polyarene templates." Pure and Applied Chemistry 89, no. 6 (2017): 809–20. http://dx.doi.org/10.1515/pac-2016-1222.

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AbstractHemispherical polyarenes represent attractive templates from which carbon nanotubes of the same diameter and rim structure (chirality) might be grown by repetitive annulation reactions. The resulting single-index (n,m) nanotubes would have one end open and the other end capped by the original template. Efforts in the author’s laboratory to synthesize (5,5) and (6,6) nanotube end-caps are described. Nitroethylene is shown to serve well as a “masked acetylene” for the conversion of polyarene bay regions into new unsubstituted benzene rings by a Diels-Alder cycloaddition/aromatization pro
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13

Adams, Harry, D. Neville Jones, Maria C. Aversa, Paola Bonaccorsi, and Placido Giannetto. "Control of stereochemistry by sulfoxide chirality in Diels-Alder reactions of 1-methoxy-3-alkylsulfinylbutadienes." Tetrahedron Letters 34, no. 40 (1993): 6481–84. http://dx.doi.org/10.1016/0040-4039(93)85076-9.

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14

ADAMS, H., D. N. JONES, M. C. AVERSA, P. BONACCORSI, and P. GIANNETTO. "ChemInform Abstract: Control of Stereochemistry by Sulfoxide Chirality in Diels-Alder Reactions of 1-Methoxy-3-alkylsulfinylbutadienes." ChemInform 25, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199416057.

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15

Jung, Michael E., and Sun-Joon Min. "Intramolecular Diels−Alder Reactions of Optically Active Allenic Ketones: Chirality Transfer in the Preparation of Substituted Oxa-Bridged Octalones." Journal of the American Chemical Society 127, no. 31 (2005): 10834–35. http://dx.doi.org/10.1021/ja052771e.

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16

Jung, Michael E., and Sun-Joon Min. "Intramolecular Diels−Alder Reactions of Optically Active Allenic Ketones: Chirality Transfer in the Preparation of Substituted Oxa-BridgedOctalones [J. Am. Chem. Soc.2005,127, 10834−10835]." Journal of the American Chemical Society 127, no. 46 (2005): 16338. http://dx.doi.org/10.1021/ja059918m.

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17

"Construction of Axial Chirality by Intramolecular Consecutive Dehydro-Diels–Alder Reaction." Synfacts 15, no. 01 (2018): 0036. http://dx.doi.org/10.1055/s-0037-1611447.

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