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Journal articles on the topic 'Cyclopentane derivatives'

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Published: 4 June 2021
Last updated: 12 February 2022

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1

Kotha, Sambasivarao, and Yellaiah Tangella. "Modular Approaches to Cyclopentanoids and their Heteroanalogs." Synlett 31, no. 20 (October 12, 2020): 1976–2012. http://dx.doi.org/10.1055/a-1288-8240.

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AbstractCyclopentanoids and their derivatives are interesting targets in synthetic organic chemistry due to their extensive applications in various branches of chemical sciences like pharmaceuticals, natural and non-natural products. In view of these applications, several synthetic strategies have been developed in the past three to four decades. In this article, we describe our work towards the synthesis of cyclopentanoids and their heteroanalogs involving diverse synthetic strategies during the past two decades. Among these, photo-thermal olefin metathesis, ring-closing metathesis, ring-rearrangement metathesis, cyclopentane annulation, [2+2+2] cycloaddition and Diels–Alder reactions have been used to assemble cyclopentane rings of diverse architecture. 1 Introduction 2 Synthesis of Spiro[4.4]nonane (A1) Derivatives 3 Synthesis of Octahydropentalene (A2) Derivatives 4 Synthesis of Linear Triquinanes (A3) 5 Synthesis Spiro Triquinanes (A4) 6 Synthesis of Angular Triquinane (A5) Systems 7 Synthesis of Hexahydro-2′H-spiro[cyclopentane-1,1′-pentalene] (A6) Ring System 8 Synthesis of Dispiro[4.1.47.25]tridecane (A7) Ring System 9 Synthesis of Hexahydro-1H-3a,7a-propanoindene Ring System10 Synthesis of Linear Tetraquinanes (A11 and A12)11 Synthesis of Tetrahydro-1′H,3′H-dispiro[cyclopentane-1,2′-pentalene-5′,1′′-cyclopentane] (A13) Ring System12 Synthesis of Decahydro-1H,8H-dicyclopenta[a,h]pentalene (A14) Ring System13 Synthesis of Dodecahydro-1H-dicyclopenta[a,d]pentalene (A15) Ring System14 Synthesis of Octahydro-1′H-spiro[cyclopentane-1,2′-cyclopenta[c]pentalene] (A16) Ring System15 Synthesis of Decahydrospiro[cyclopentane-1,7′-cyclopenta-[a]pentalene] (A17) Ring System16 Synthesis of Compact Tetraquinane (A18)17 Synthesis of Higher Polyquinanes18 Conclusions19 Acronyms
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2

Manna, Madhu Sudan, and Santanu Mukherjee. "Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes." Organic & Biomolecular Chemistry 13, no. 1 (2015): 18–24. http://dx.doi.org/10.1039/c4ob01649a.

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Asymmetric desymmetrization represents an excellent strategy for obtaining highly functionalized chiral building blocks. However, the application of this strategy for the synthesis of cyclopentane derivatives remained limited, when compared to cyclohexanes. Here, we give an overview of asymmetric desymmetrization reactions leading to enantioenriched cyclopentanes.
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3

Allan, RD, and J. Fong. "Synthesis of Analogs of GABA .15. Preparation and Resolution of Some Potent Cyclopentene and Cyclopentane Derivatives." Australian Journal of Chemistry 39, no. 6 (1986): 855. http://dx.doi.org/10.1071/ch9860855.

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A series of cyclopentene and cyclopentane analogues of GABA has been prepared utilizing a thermal cis -trans isomerization of the phthalimido β,γ -unsaturated acid (10) as the key step to obtain trans-4- aminocyclopent-2-ene-1-carboxylic acid (7). Resolution of some of the potent GABA analogues, in particular (+)-(4S)- and (-)-(4R)-4- aminocyclopent-1-ene-1-carboxylic acid (5), has been achieved by crystallization of isopropylideneribonolactone esters or pantolactone esters of the phthalimido -protected intermediates.
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4

KOJIMA, KOICHI, SHIGEO AMEMIYA, HIROSHI SUEMUNE, and KIYOSHI SAKAI. "Stereospecific synthesis of functionalized cyclopentane derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 7 (1985): 2750–61. http://dx.doi.org/10.1248/cpb.33.2750.

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5

Kazakova, Oxana B., Elena V. Tretyakova, Irina E. Smirnova, Timur I. Nazyrov, Ol'ga S. Kukovinets, Genrikh A. Tolstikov, and Kiryll Yu Suponitskii. "An Efficient Oxyfunctionalization of Quinopimaric Acid Derivatives with Ozone." Natural Product Communications 8, no. 3 (March 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800304.

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An access to oxyfunctionalized quinopimaric acid derivatives is reported. The ozonolysis of methyl dihydroquinopimarate occurs through 1,2-cycloaddition of ozone to the bridging double bond followed by intermolecular rearrangements and formation of nontrivial 4β-hydroxy-4α,14α-epoxy-13(15)-ene derivative 2. The oxidation of methyl furfurilydene dihydroquinopimarate with ozone led to anhydride 5 and unexpected carboxymethyl substituted cyclopentane lactone 6. The structure of compound 6 was confirmed by X-Ray analysis of its methyl ester.
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6

Campbell, M., DJ Collins, and AM James. "Synthesis of 2-(5',5'-Ethylenedioxy-1'-methylcyclopent-2'-en-1'-yl)ethanol, and Some 2H-Cyclopenta[b]furan Derivatives Formed by Intramolecular Displacement Reactions." Australian Journal of Chemistry 42, no. 1 (1989): 17. http://dx.doi.org/10.1071/ch9890017.

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Exchange dioxolanation of 2-methyl-2-(prop-2′-enyl)cyclopentane-1,3-done (1b) gave 3,3- ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopentan-1-one (2) which, upon reduction and esterification , afforded the epimeric 3,3-ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopent-1-yl benzoates (6d). Oxidative cleavage of the terminal double bond in (6d),followed by sodium borohydride reduction yielded 3,3-ethylenedioxy-2-(2'-hydroxyethyl)-2-methylcyclopent-1-yl benzoate (4b) which underwent acid- catalysed rearrangement to 6a-(2′-hydroxyethoxy)-3a- methylhexahydrocyclopenta [b]furan-4-yl benzoate (8b). Flash vacuum pyrolysis of the t- butyldimethylsilyl ether (12), derived from the hydroxy acetal (4b), afforded 3-[2′- (t- butyldimethylsilyloxy )ethyl]-4,4-ethy1enedioxy-3-methylcyclopent-1-ene (14) which upon selective cleavage of the silyl ether group gave 2-(5′,5′-ethylenedioxy-1′-methylcyclopent- 2'′en-1′-y1)ethanol (7). Reaction of the mesylate (16) of (7) with lithium bromide or iodide in tetrahydrofuran at 50-55� for several hours yielded some of the corresponding 3-(2′-haloethyl) compounds (17), but gave mainly the rearranged 6a-(2′-haloethoxy)-3a-methyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furans (19a) and (19b). Some related chemistry is described.
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7

Manchado, Alejandro, Victoria Elena Ramos, David Díez, and Narciso M. Garrido. "Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products." Molecules 25, no. 6 (March 13, 2020): 1308. http://dx.doi.org/10.3390/molecules25061308.

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The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.
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8

Desai, Ranjit C., Peter Cicala, Laura C. Meurer, and Paul E. Finke. "Expeditious synthesis of tri-substituted cyclopentane derivatives." Tetrahedron Letters 43, no. 26 (May 2002): 4569–70. http://dx.doi.org/10.1016/s0040-4039(02)00901-2.

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9

Bauman, L. E., and J. Laane. "Pseudorotation of cyclopentane and its deuterated derivatives." Journal of Physical Chemistry 92, no. 5 (March 1988): 1040–51. http://dx.doi.org/10.1021/j100316a011.

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10

Lin, Yan, Qijun Wang, Yang Wu, Chang Wang, Hao Jia, Cheng Zhang, Jiaxing Huang, and Hongchao Guo. "Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides." RSC Advances 8, no. 71 (2018): 40798–803. http://dx.doi.org/10.1039/c8ra08881k.

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11

Prajapti, Santosh Kumar, Shweta Shrivastava, Umesh Bihade, Ajay Kumar Gupta, V. G. M. Naidu, Uttam Chand Banerjee, and Bathini Nagendra Babu. "Synthesis and biological evaluation of novel Δ2-isoxazoline fused cyclopentane derivatives as potential antimicrobial and anticancer agents." MedChemComm 6, no. 5 (2015): 839–45. http://dx.doi.org/10.1039/c4md00525b.

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12

Sun, Yan, Jing Sun, and Chao-Guo Yan. "Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione." Beilstein Journal of Organic Chemistry 9 (January 3, 2013): 8–14. http://dx.doi.org/10.3762/bjoc.9.2.

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A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.
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13

Leemans, Erika, Matthias D’hooghe, and Norbert De Kimpe. "Ring Expansion of Cyclobutylmethylcarbenium Ions to Cyclopentane or Cyclopentene Derivatives and Metal-Promoted Analogous Rearrangements." Chemical Reviews 111, no. 5 (May 11, 2011): 3268–333. http://dx.doi.org/10.1021/cr100295j.

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14

Cordier, Marie, Aurélie Dos Santos, Laurent El Kaïm, and Noisette Narboni. "Passerini/Tsuji–Trost strategies towards achieving lactams and cyclopentane derivatives." Chemical Communications 51, no. 29 (2015): 6411–14. http://dx.doi.org/10.1039/c5cc00584a.

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15

Guo, Hua Mei, Qian Wu, and Yu Feng Li. "Synthesis and Crystal Structure Studies on 6-Amino-5,5,7-Tricyano-3,3a,4,5-Tetrahydro-2H-Indene-4-Spirocyclopentane." Advanced Materials Research 1025-1026 (September 2014): 717–22. http://dx.doi.org/10.4028/www.scientific.net/amr.1025-1026.717.

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A malononitrile derivative, 6-Amino-5,5,7-tricyano-3,3a,4,5-tetrahydro-2H-indene-4- Spirocyclopentane was synthesized in ethanol with malononitrile and cyclopentanone as raw materials. It was characterized by X-ray single crystal diffraction analysis.The crystal of the title complex belongs to Triclinic, P21/c space group with a=6.4687(13)Å, b=8.9901(18)Å, c=12.004(2)Å, α=93.55(3) deg, β=91.86(3) deg, γ=92.25(3) deg. V=695.8(2)Å3, Z=2, F(000)=278 and final R1=0.0524,WR2=0.1497. X-ray analysis reveals that The cyclohexene ring has a distorted half-chair conformation and the cyclopentene and cyclopentane rings adopt envelope conformations. The dihedral angles between planar fragments of the cyclohexene and cyclopentene rings and of the cyclohexene and cyclopentane rings are 10.67 (7) and 87.33 (3)°, respectively. In the crystal, intermolecular N-HN hydrogen bonds link the molecules into infinite chains running in the [10] direction.
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16

Mitani, Michiharu, Hiroshi Takeuchi, and Kikuhiko Koyama. "Synthesis of Cyclopentane Derivatives by Electrochemical Reduction of 1,5-Dibromopentane Derivatives." Chemistry Letters 15, no. 12 (December 5, 1986): 2125–26. http://dx.doi.org/10.1246/cl.1986.2125.

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17

Kelch, André S., Peter G. Jones, Ina Dix, and Henning Hopf. "The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives." Beilstein Journal of Organic Chemistry 9 (August 19, 2013): 1705–12. http://dx.doi.org/10.3762/bjoc.9.195.

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With the goal of eventually synthesizing [5]radialene (3), the still missing member of the parent radialene hydrocarbons, we have prepared the pentaacetates 21 and 31, the pentabromide 29 and the hexabromide 32. In principle these should be convertible by elimination reactions to the desired target molecule.
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18

Lacerda, Valdemar, Gil V. J. da Silva, Mauricio G. Constantino, Cláudio F. Tormena, R. Thomas Williamson, and Brian L. Marquez. "Long-rangeJCH heteronuclear coupling constants in cyclopentane derivatives." Magnetic Resonance in Chemistry 44, no. 1 (2005): 95–98. http://dx.doi.org/10.1002/mrc.1723.

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19

Csuk, René, Petra Dörr, Martin Kühn, Claus Krieger, Hermann Irngartinger, Thomas Oeser, and Mikhael Yu Antipin. "Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, II." Zeitschrift für Naturforschung B 54, no. 8 (August 1, 1999): 1079–91. http://dx.doi.org/10.1515/znb-1999-0817.

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Suitable protected 4,4a-anhydro-cyclopentane derivatives have been used for the straightforward of cyclopentanoid nucleoside precursors. Thus, by simple transformations nucleoside precursors modified at the positions C(4), C(4a) and C(4,4a) as well as side-chain modified derivatives were accessible. The structures of the key intermediates were determined by xray analyses.
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20

Gimazetdinov, Airat M., Nadezhda A. Ivanova, and Mansur S. Miftakhov. "A New Approach to the Synthesis of Chiral Blocks for Cyclopentanoids." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800725.

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A microreview is presented of the development by the authors of the original preparation of enantiomerically pure cyclopentane blocks from the racemic [2+2]-cycloadducts of 1,3-cyclopentadiene and its derivatives with dichloroketene.
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21

Llona-Minguez, Sabin, and Simon P. Mackay. "Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)." Beilstein Journal of Organic Chemistry 10 (June 11, 2014): 1333–38. http://dx.doi.org/10.3762/bjoc.10.135.

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A convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chiral cyclopentane-1,2-diol and -1,2,3-triol derivatives. This unusual substitution pattern provides a useful starting point for the discovery of novel bioactive molecules.
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22

Verma, Kamal, Irshad Maajid Taily, and Prabal Banerjee. "Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives." Organic & Biomolecular Chemistry 17, no. 35 (2019): 8149–52. http://dx.doi.org/10.1039/c9ob01369e.

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An efficient method for the synthesis of spiro-cyclopentane benzofuran derivatives via a MgI2-catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes in good yield has been developed.
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23

Desai, Ranjit C., Peter Cicala, Laura C. Meurer, and Paul E. Finke. "ChemInform Abstract: Expeditious Synthesis of Tri-Substituted Cyclopentane Derivatives." ChemInform 33, no. 40 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200240104.

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24

Moriarty, Robert M., Neena Rani, Eric J. May, and Liang Guo. "Functionalization of Fused Cyclopentane Derivatives using Hypervalent Iodine Reagents†." Journal of Chemical Research, no. 1 (1998): 32–33. http://dx.doi.org/10.1039/a701440f.

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25

Hinz, Alexander, Axel Schulz, and Alexander Villinger. "Zwitterionic and biradicaloid heteroatomic cyclopentane derivatives containing different group 15 elements." Chemical Science 7, no. 1 (2016): 745–51. http://dx.doi.org/10.1039/c5sc03515e.

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The formal cyclopentane-1,3-diyl derivatives [E1(μ-NTer)2({E2C} = NDmp)] (Ter = 2,6-dimesityl-phenyl, Dmp = 2,6-dimethylphenyl) were prepared by 1,1-insertion of CNDmp into the N–E2 bond of [E1(μ-NTer)2E2] (E1 = N, P; E2 = P, As).
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26

Kavrakova, Ivanka K. "Lewis acid promoted radical annulation reaction of 2-bromopentenoyl-2-oxazolidinones with 1-hexene." Journal of Chemical Research 2005, no. 10 (October 2005): 682–84. http://dx.doi.org/10.3184/030823405774663174.

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Radical Lewis acid promoted annulation reaction of 2-bromopentenoyl-2-oxazolidinones with 1-hexene proceeded smoothly under mild conditions to give functionalised cyclopentane derivatives in good yield but with modest diastereoselectivity. Reductive debromination with tris(trimethylsilyl)silane, LiOOH hydrolysis and esterification provided cleanly the corresponding cyclopentaneacetic acid and its methyl ester.
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27

Dai, Chenlu, Mingshuang Li, Mengjun Chen, Naili Luo, and Cunde Wang. "Novel synthesis of highly functionalized cyclopentane derivatives via [3 + 2] cycloaddition reactions of donor–acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates." Journal of Chemical Research 43, no. 1-2 (January 2019): 43–49. http://dx.doi.org/10.1177/1747519819831883.

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An efficient [3 + 2] cycloaddition reaction of cyanocyclopropanecarbonates and ( E)-3-aryl-2-cyanoacrylates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene for the synthesis of highly functionalized cyclopentane derivatives in moderate to good yields (79%−87%) was developed. The structures of two typical products were confirmed by X-ray crystallography.
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28

Yamaura, Yousuke, and Miwako Mori. "Enantioselective synthesis of cyclopentane derivatives using zirconium-catalyzed asymmetric cyclization." Tetrahedron Letters 40, no. 16 (April 1999): 3221–24. http://dx.doi.org/10.1016/s0040-4039(99)00472-4.

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29

Díaz, Miguel, Javier Ibarzo, and Rosa M. Ortuño. "Stereoselective synthesis of new homochiral polyfunctional side-chain cyclopentane derivatives." Tetrahedron: Asymmetry 5, no. 1 (January 1994): 37–40. http://dx.doi.org/10.1016/s0957-4166(00)80480-2.

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30

Chand, Pooran, Y. Sudhakar Babu, Shanta Bantia, Scott Rowland, Ali Dehghani, Pravin L. Kotian, Tracy L. Hutchison, et al. "Syntheses and Neuraminidase Inhibitory Activity of Multisubstituted Cyclopentane Amide Derivatives." Journal of Medicinal Chemistry 47, no. 8 (April 2004): 1919–29. http://dx.doi.org/10.1021/jm0303406.

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31

Lacerda, Valdemar, Gil V. J. da Silva, Cláudio F. Tormena, R. Thomas Williamson, and Brian L. Marquez. "Long-rangeJCH heteronuclear coupling constants in cyclopentane derivatives. Part II." Magnetic Resonance in Chemistry 45, no. 1 (2006): 82–86. http://dx.doi.org/10.1002/mrc.1912.

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32

Weinges, By Klaus, and Wolfgang Sipos. "A Novel Route to Cyclopentane Derivatives: A Radical Chain Reaction." Angewandte Chemie International Edition in English 26, no. 11 (November 1987): 1152–53. http://dx.doi.org/10.1002/anie.198711521.

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33

Leemans, Erika, Matthias D'Hooghe, and Norbert De Kimpe. "ChemInform Abstract: Ring Expansion of Cyclobutylmethyl Carbenium Ions to Cyclopentane and Cyclopentene Derivatives and Metal-Promoted Analogous Rearrangement." ChemInform 42, no. 36 (August 11, 2011): no. http://dx.doi.org/10.1002/chin.201136230.

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34

Hiroi, Kunio, and Yoshihisa Arinaga. "Transition metal-catalyzed asymmetric vinylcyclopropane-cyclopentene rearrangements. Asymmetric synthesis of cyclopentane derivatives using chiral sulfoxides as chiral sources." Tetrahedron Letters 35, no. 1 (January 1994): 153–56. http://dx.doi.org/10.1016/0040-4039(94)88188-x.

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35

Witt, Matthias, Dirk Kreft, and Hans-Friedrich Grützmacher. "Effects of Internal Hydrogen Bonds between Amide Groups: Protonation of Alicyclic Diamides." European Journal of Mass Spectrometry 9, no. 2 (April 2003): 81–95. http://dx.doi.org/10.1255/ejms.535.

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The proton affinity ( PA) of cyclopentane carboxamide 1, cyclohexane carboxamide 2 and their secondary and tertiary amide derivatives S1, S2, T1 and T2, was determined by the thermokinetic method and the kinetic method [ PA(1) = 888 ± 5 kJ mol−1; PA(2) = 892 ± 5 kJ mol−1; PA(S1) = 920 ± 6 kJ mol−1; PA(S2) = 920 ± 6 kJ mol−1; PA(T1) = 938 ± 6 kJ mol−1; PA(T2) = 938 ± 6 kJ mol−1]. Special entropy effects are not observed. Additionally, the effects of protonation have been studied using an advanced kinetic method for all isomers 3–7 of cyclopentane dicarboxamides and cyclohexane dicarboxamides (with the exception of cis-cyclopentane-1,2-dicarboxamide) and their bis-tertiary derivatives T3–T7 by estimating the PA and the apparent entropy of protonation Δ(Δ Sapp). Finally, the study was extended to bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxamide 8 and its bis-tertiary derivative T8, to all stereoisomers of bicyclo[2.2.1]heptane-2,3-dicarboxamide 9, their secondary and tertiary amide derivatives S9 and T9, and to endo–endo–bicyclo[2.2.1]heptane-2,5-dicarboxamide 10 and the corresponding secondary and tertiary derivatives S10 and T10. Compared with 1 and 2, all alicyclic diamides exhibit a significant increase of the PA (ΔPA) and special entropy effects on protonation. For alicyclic diamides, which can not accommodate a conformation appropriate for building a proton bridge, the values of Δ PA and Δ(Δ Sapp) are small to moderate. This is explained by ion / dipole interactions between the protonated and neutral amide group which stabilize the protonated species but hinder the free rotation of the amide groups. If any of the conformations of the alicyclic diamide allows formation of a proton bridge, Δ PA and Δ(Δ Sapp) increase considerably. A spectacular case is cis-cyclohexane-1,4-dicarboxamide 7c which is the most basic monocyclic diamide, although generation of the proton bridge requires the unfavorable boat conformation with both amide substituents at a flagpole position. A pre-orientation of the two amide groups in such a 1,4-position in 10 results in a particularly large PA of < 1000 kJ mol−1. The observation of comparable values for Δ(Δ Sapp) for linear and monocyclic diamides indicates that a major part of the entropy effects originates from freezing the free rotation of the amide groups by formation of the proton bridge. This is corroborated by observing corresponding effects during the protonation of dicarboxamides containing the rigid bicyclo[2.2.1]heptane carbon skeleton, where the only internal movements of the molecules corresponds to rotation of the amide substituents.
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36

Zulfiqar, Fazila, and Abdul Malik. "Facile Approach to Versatile Chiral Intermediates for Fused Cyclopentanoid Natural Products." Zeitschrift für Naturforschung B 56, no. 11 (November 1, 2001): 1227–34. http://dx.doi.org/10.1515/znb-2001-1119.

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A facile approach to cis- and trans-2-(l-hydroxymethyl)vinyl-1-vinylcyclohexan-1-ols and to the corresponding cyclopentane, cycloheptane, and cyclooctane derivatives has been developed, starting from cycloalkanones involving the key steps of Rupe and Claisen orthoester rearrangements. The formation of intervening products could be explained by allylic strain and π-stacking, respectively.
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37

Lowinger, Timothy B., and Larry Weiler. "The consecutive cyclization–elimination reaction of a radical generated from an epoxide: stereospecific formation of an exocyclic alkene." Canadian Journal of Chemistry 68, no. 9 (September 1, 1990): 1636–37. http://dx.doi.org/10.1139/v90-253.

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A titanium(III) mediated radical cyclization–elimination reaction is reported, which allows for the efficient generation of functionalized cyclopentane derivatives. The reaction is highly stereospecific, giving excellent control over the geometry of the resulting exocyclic alkene. In addition, functionality at both reacting termini is retained for subsequent transformations. Keywords: stereospecific, radical cyclization–elimination, exocyclic alkene.
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38

Vatsadze, Sergey Z., Marina A. Manaenkova, Evgeny V. Vasilev, Nikolai U. Venskovsky, and Victor N. Khrustalev. "Crystal structures and supramolecular features of 9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone, 3,7-diazaspiro[bicyclo[3.3.1]nonane-9,1′-cyclopentane]-2,4,6,8-tetraone and 9-methyl-9-phenyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone dimethylformamide monosolvate." Acta Crystallographica Section E Crystallographic Communications 73, no. 7 (June 30, 2017): 1097–101. http://dx.doi.org/10.1107/s2056989017009458.

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Compounds (I), C9H10N2O4, (II), C11H12N2O4, and (III), C14H12N2O4·C3H7NO represent 9,9-disubstituted-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone derivatives with very similar molecular geometries for the bicyclic framework: the dihedral angle between the planes of the imide groups is 74.87 (6), 73.86 (3) and 74.83 (6)° in (I)–(III), respectively. The dimethyl derivative (I) is positioned on a crystallographic twofold axis and its overall geometry deviates only slightly from idealizedC2vsymmetry. The spiro-cyclopentane derivative (II) and the phenyl/methyl analog (III) retain only internalCssymmetry, which in the case of (II) coincides with crystallographic mirror symmetry. The cyclopentane moiety in (II) adopts an envelope conformation, with the spiro C atom deviating from the mean plane of the rest of the ring by 0.548 (2) Å. In compound (III), an N—H...O hydrogen bond is formed with the dimethylformamide solvent molecule. In the crystal, both (I) and (II) form similar zigzag hydrogen-bonded ribbons through double intermolecular N—H...O hydrogen bonds. However, whereas in (I) the ribbons are formed by twotrans-arranged O=C—N—H amide fragments, the amide fragments arecis-positioned in (II). The formation of ribbons in (III) is apparently disrupted by participation of one of its N—H groups in hydrogen bonding with the solvent molecule. As a result, the molecules of (III) form zigzag chains rather than the ribbons through intermolecular N—H...O hydrogen bonds. The crystal of (I) was a pseudo-merohedral twin.
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39

Veits, Gesine K., Donald R. Wenz, Leoni I. Palmer, André H. St. Amant, Jason E. Hein, and Javier Read de Alaniz. "Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives." Organic & Biomolecular Chemistry 13, no. 31 (2015): 8465–69. http://dx.doi.org/10.1039/c5ob00944h.

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The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.
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40

Wang, Liang, Jie Gao, Lirong Wan, Ying Wang, and Changsheng Yao. "Electrocatalytic multicomponent transformation of cyclopentane-1,3-dione, aldehydes and malononitrile: an efficient way to cyclopenta[b]pyran derivatives." Research on Chemical Intermediates 41, no. 5 (September 14, 2013): 2775–84. http://dx.doi.org/10.1007/s11164-013-1387-6.

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41

Miao, Zhiwei, Weiping Zheng, Yuming Li, Jiayong Zhang, and Siyi Du. "Highly Regio- and Diastereoselective [3+2]-Annulation Reaction of Morita–Baylis–Hillman Carbonates with Pyrazolones Catalyzed by Tertiary Phosphines." Synthesis 49, no. 16 (May 18, 2017): 3676–85. http://dx.doi.org/10.1055/s-0036-1589030.

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A phosphine-catalyzed [3+2] annulation between N-phenylpyrazolone derivatives and Morita–Baylis–Hillman carbonates for the synthesis of chiral heterocyclic systems containing spiro[cyclopentane-3,3′-pyrazole] scaffolds has been developed. The reaction afforded the desired products in moderate to high yields (up to 97%) with good to excellent diastereoselectivities (up to 20:1). A plausible reaction mechanism has also been proposed based on previous literature.
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42

Hatvate, Navnath T., Shrikant M. Ghodse, Krishna N. Mundlod, and Vikas N. Telvekar. "Metal-Free Synthesis of Pyrimidinone Derivatives via Biginelli Reaction Using Aqueous NaICl2." Letters in Organic Chemistry 17, no. 8 (August 18, 2020): 613–17. http://dx.doi.org/10.2174/1570178617666191126095808.

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Metal-free synthesis of pyrimidinone (alky/aryl) via Biginelli reaction in the presence of aqueous sodium dichloroiodate (NaICl2) was studied under reflux conditions. Herein, we first time report the synthesis of the aliphatic Biginelli product by using aliphatic aldehyde, cyclopentane, and urea. Several aromatic and heteroaromatic aldehydes were studied for the confirmation of the wide applicability of aq. NaICl2 for the synthesis of corresponding Biginelli products. The obtained desired products provide good to excellent yield.
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43

Benke, Zsanett, Attila M. Remete, and Loránd Kiss. "A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines." Beilstein Journal of Organic Chemistry 17 (August 13, 2021): 2051–66. http://dx.doi.org/10.3762/bjoc.17.132.

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This work presents an examination of the selective functionalization of norbornadiene through nitrile oxide 1,3-dipolar cycloaddition/ring-opening metathesis (ROM)/cross-metathesis (CM) protocols. Functionalization of commercially available norbornadiene provided novel bicyclic scaffolds with multiple stereogenic centers. The synthesis involved selective cycloadditions, with subsequent ROM of the formed cycloalkene-fused isoxazoline scaffolds and selective CM by chemodifferentiation of the olefin bonds of the resulting alkenylated derivatives. Various experimental conditions were applied for the CM transformations with the goal of exploring substrate and steric effects, catalyst influence and chemodifferentiation of the olefin bonds furnishing the corresponding functionalized, fluorine-containing isoxazoline derivatives.
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44

Ali, Syed Masarrat, and Gérard Rousseau. "Formation of Cyclopentane Derivatives by Mukaiyama's Reaction of Bisketene Silyl Acetals." Synlett 1990, no. 07 (1990): 397–98. http://dx.doi.org/10.1055/s-1990-21104.

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45

Lacerda, Valdemar, Gil V. J. da Silva, Mauricio G. Constantino, Cláudio F. Tormena, R. Thomas Williamson, and Brian L. Marquez. "Erratum: Long-rangeJCH heteronuclear coupling constants in cyclopentane derivatives. Part II." Magnetic Resonance in Chemistry 45, no. 3 (2007): 282. http://dx.doi.org/10.1002/mrc.1980.

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46

Constantino, Mauricio Gomes, Valdemar Lacerda Júnior, and Gil Valdo José da Silva. "Detailed assignments of1H and13C NMR spectral data of 14 cyclopentane derivatives." Magnetic Resonance in Chemistry 41, no. 8 (July 2, 2003): 641–43. http://dx.doi.org/10.1002/mrc.1221.

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47

MORIARTY, R. M., N. RANI, E. J. MAY, L. GUO, and O. PRAKASH. "ChemInform Abstract: Functionalization of Fused Cyclopentane Derivatives Using Hypervalent Iodine Reagents." ChemInform 30, no. 6 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199906075.

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48

Gu, Ze-Bin, Hai-Xia Lin, Yong-Mei Cui, Min-Jie Li, and Zeng-Shuai Hao. "Synthesis and characterization of 2′,7′-diarylspiro[cyclopentane-1,9′-fluorene] derivatives." Monatshefte für Chemie - Chemical Monthly 146, no. 9 (February 25, 2015): 1519–27. http://dx.doi.org/10.1007/s00706-015-1432-9.

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49

Henry-Riyad, Huda, and Thomas T. Tidwell. "Cyclization of 5-hexenyl radicals from nitroxyl radical additions to 4-pentenylketenes and from the acyloin reaction." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 697–704. http://dx.doi.org/10.1139/v03-076.

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Photochemical Wolff rearrangements were used to form 5-substituted-4-pentenylketenes 1a–1d (RCH=CHCH2XCH2CH=C=O: 1a R = H, X = CH2; 1b R = Ph, X = CH2; 1c R = c-Pr, X = CH2; 1d R = H, X = O), which were observed by IR at 2121, 2120, 2119, and 2126 cm–1, respectively, as relatively long-lived species at room temperature in hydrocarbon solvents. These reacted with the nitroxyl radical tetramethylpiperidinyloxyl (TEMPO, TO·) forming carboxy-substituted 5-hexenyl radicals 3, which were trapped by a second nitroxyl radical forming 1,2 diaddition products 4a–4d. On thermolysis, 4a–4d underwent reversible reformation of the radicals 3, which underwent cyclization forming cyclopentanecarboxylic acid derivatives 6 or 11 as the major products. However, in the case of 1b, the cyclopentane derivative was formed reversibly and on prolonged reaction times the only product isolated was PhCH=CH-(CH2)4CO2H (8b) from hydrogen transfer to Cβ and cleavage of the TEMPO group. Cyclopropylcarbinyl radical ring opening in the cyclized radical 5c from 1c led to the 2-(4-N-tetramethylpiperidinyloxybut-1-enyl)cyclopentane derivative 11 as the major product. In a test for 5-hexenyl radical ring closure in the radical anion intermediate of the acyloin condensation, the ester CH2=CH(CH2)3CO2Et (12a) gave the acyloin 13a (76%) as the only observed product, while PhCH=CH(CH2)3CO2CH3 (12b) with Na in toluene gave 21% of the acyloin product 13b and 42% of 2-benzylcyclopentanol (15) from cyclization of the intermediate radical anion.Key words: ketenes, free radical cyclization, TEMPO, acyloin condensation.
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50

HIROI, K., and Y. ARINAGA. "ChemInform Abstract: Transition Metal Catalyzed Asymmetric Vinylcyclopropane-Cyclopentene Rearrangements. Asymmetric Synthesis of Cyclopentane Derivatives Using Chiral Sulfoxides as Chiral Sources." ChemInform 25, no. 17 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199417033.

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