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Journal articles on the topic 'Metatesi olefinica'

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Author: Grafiati

Published: 10 March 2023

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1

Patrzałek, Michał, Aleksandra Zasada, Anna Kajetanowicz, and Karol Grela. "Tandem Olefin Metathesis/α-Ketohydroxylation Revisited." Catalysts 11, no. 6 (June 9, 2021): 719. http://dx.doi.org/10.3390/catal11060719.

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EWG-activated and polar quaternary ammonium salt-tagged ruthenium metathesis catalysts have been applied in a two-step one-pot metathesis-oxidation process leading to functionalized α-hydroxyketones (acyloins). In this assisted tandem process, the metathesis catalyst is used first to promote ring-closing metathesis (RCM) and cross-metathesis (CM) steps, then upon the action of Oxone™ converts into an oxidation catalyst able to transform the newly formed olefinic product into acyloin under mild conditions.

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2

Drège, E., J. Oko, P. E. Venot, N. Gigant, and D. Joseph. "Microwave-assisted telescoped cross metathesis-ring closing aza-Michael reaction sequence: step-economical access to nicotine–lobeline hybrid analogues." RSC Advances 5, no. 117 (2015): 96720–24. http://dx.doi.org/10.1039/c5ra20930g.

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Step-economical access to nicotinic acetylcholine receptor ligands hybrids through an efficient telescoped cross-metathesis/cyclizing aza-Michael addition involving N-heteroaromatic olefinic derivatives.

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3

Fischmeister, Cédric, and Christian Bruneau. "Ene–yne cross-metathesis with ruthenium carbene catalysts." Beilstein Journal of Organic Chemistry 7 (February 4, 2011): 156–66. http://dx.doi.org/10.3762/bjoc.7.22.

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Conjugated 1,3-dienes are important building blocks in organic and polymer chemistry. Enyne metathesis is a powerful catalytic reaction to access such structural domains. Recent advances and developments in ene–yne cross-metathesis (EYCM) leading to various compounds of interest and their intermediates, that can directly be transformed in tandem procedures, are reviewed in this article. In addition, the use of bio-resourced olefinic substrates is presented.

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4

Postema, Maarten H. D., and Jared L. Piper. "Cross-metathesis and ring-closing metathesis of olefinic monosaccharides." Tetrahedron Letters 43, no. 39 (September 2002): 7095–99. http://dx.doi.org/10.1016/s0040-4039(02)01617-9.

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5

Balcar, Hynek, and Jiří Čejka. "SBA-15 as a Support for Effective Olefin Metathesis Catalysts." Catalysts 9, no. 9 (September 2, 2019): 743. http://dx.doi.org/10.3390/catal9090743.

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Olefin metathesis is the catalytic transformation of olefinic substrates, finding a wide range of applications in organic synthesis. The mesoporous molecular sieve Santa Barbara Amorphous (SBA-15) has proven to be an excellent support for metathesis catalysts thanks to its regular mesoporous structure, high BET area, and large pore volume. A survey of catalysts consisting of (i) molybdenum and tungsten oxides on SBA-15, and (ii) molybdenum and ruthenium organometallic complexes (Schrock and Grubbs-type carbenes) on SBA-15 is provided together with their characterization and catalytic performance in various metathesis reactions. The comparison with catalysts based on other supports demonstrates the high quality of the mesoporous molecular sieve SBA-15 as an advanced catalyst support.

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6

Kotha, Sambasivarao, and Mirtunjay Kumar Dipak. "Design and synthesis of novel bis-annulated caged polycycles via ring-closing metathesis: pushpakenediol." Beilstein Journal of Organic Chemistry 10 (November 13, 2014): 2664–70. http://dx.doi.org/10.3762/bjoc.10.280.

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Intricate caged molecular frameworks are assembled by an atom economical process via a Diels–Alder (DA) reaction, a Claisen rearrangement, a ring-closing metathesis (RCM) and an alkenyl Grignard addition. The introduction of olefinic moieties in the pentacycloundecane (PCUD) framework at appropriate positions followed by RCM led to the formation of novel heptacyclic cage systems.

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7

Krishna, Palakodety, Govinda Kundoor, and Suresh Battina. "A Concise and Stereoselective Total Synthesis of Pestalotioprolide C Using Ring-Closing Metathesis." Synthesis 50, no. 05 (December 20, 2017): 1152–58. http://dx.doi.org/10.1055/s-0036-1589152.

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The stereoselective total synthesis of the pestalotioprolide C is disclosed in 13 linear steps in 4% overall yield. The key steps in this approach are a ring-closing-metathesis protocol for the construction of the 14-membered macrolide with E-olefinic bond, a Keck allylation, and a Sharpless kinetic resolution for the installation of desired stereocenters at C4 and C7.

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8

Ramnauth, Jailall, and Edward Lee-Ruff. "Photocycloelimination of α,α-dichlorocyclobutanones." Canadian Journal of Chemistry 77, no. 7 (July 1, 1999): 1245–48. http://dx.doi.org/10.1139/v99-110.

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Direct irradiation of a series of α,α-dichlorocyclobutanones in benzene solutions results in photocycloelimination to give 1,1-dichloroalkenes in yields ranging from 30-65%. The α,α-dichlorocyclobutanones were formed in good yields from the [2+2] cycloaddition of the terminal olefins with dichloroketene. This two-step sequence formally represents a "metathesis" of two olefinic functions and provides an easy access to functionalized 1,1-dichloroalkenes. Irradiation of the dichlorocyclobutanones in the solid state led to poor yields of 1,1-dichloroalkenes and polymeric mixtures, however, photoreactions performed in zeolites gave similar yields as those run in benzene solutions.Key words: dichlorocyclobutanones, dichloroalkenes, olefin metathesis, photocycloelimination.

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9

Chen, Cong-Yan, and Dennis J. O'Rear. "Disproportionation of Alkanes via Molecular Redistribution and Molecular Averaging." Collection of Czechoslovak Chemical Communications 73, no. 8-9 (2008): 1105–11. http://dx.doi.org/10.1135/cccc20081105.

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In this paper the disproportionation of alkanes via molecular redistribution (MR) and molecular averaging (MA) is discussed. MR/MA chemistry consists of three steps occurring in one single catalyst bed over a bifunctional catalyst system: dehydrogenation of alkanes to olefinic intermediates, metathesis (disproportionation) of these olefin species and hydrogenation of the metathesis products to alkanes. MR/MA represents a unique and rare example of bifunctional heterogeneous catalysis while there are many examples of acid components being one of the bifunctional elements with a metal, e.g., in reforming, hydrocracking and isomerization reactions. MR/MA chemistry provides simple processes which can be accomplished otherwise only via combinations of other existing chemistries. In this paper, we will use MR of pentanes as an example to demonstrate one industrial application of the MR chemistry.

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10

Andreana, Peter R., Jason S. McLellan, Yongchen Chen, and Peng George Wang. "Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis." Organic Letters 4, no. 22 (October 2002): 3875–78. http://dx.doi.org/10.1021/ol026710m.

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11

Berezowska, Irena, Nga N. Chung, Carole Lemieux, Brian C. Wilkes, and Peter W. Schiller. "Cyclic dermorphin tetrapeptide analogues obtained via ring-closing metathesis." Acta Biochimica Polonica 53, no. 1 (February 23, 2006): 73–76. http://dx.doi.org/10.18388/abp.2006_3363.

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The dermorphin-derived cyclic tetrapeptide analogues H-Tyr-c[D-Cys-Phe-Cys]NH(2) and H-Tyr-c[D-Cys-Phe-D-Cys]NH(2) are opioid agonists at the mu and delta receptor. To enhance the metabolic stability of these peptides, we replaced the disulfide bridge with a bis-methylene moiety. This was achieved by solid-phase synthesis of the linear precursor peptide containing allylglycine residues in place of the Cys residues, followed by ring-closing metathesis. In the case of the peptide with L-configuration in the 4-position both the cis and the trans isomer of the resulting olefinic peptides were formed, whereas the cis isomer only was obtained with the peptide having the D-configuration in position 4. Catalytic hydrogenation yielded the saturated -CH(2)-CH(2)- bridged peptides. In comparison with the cystine-containing parent peptides, all olefinic peptides showed significantly reduced mu and delta agonist potencies in the guinea pig ileum and mouse vas deferens assays. The -CH(2)-CH(2)-bridged peptide with l-configuration in the 4-position was equipotent with its cystine-containing parent in both assays, whereas the bis-methylene analogue with D-configuration in position 4 was 10-27-fold less potent compared to its parent. The effect of the disulfide replacements with the -CH=CH- and -CH(2)-CH(2)- moieties on the conformational behavior of these peptides was examined by theoretical conformational analysis which provided plausible explanations in terms of structural parameters for the observed changes in opioid activity.

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12

Greish, Alexander A., Leonid M. Kustov, and Alexander V. Vasnev. "Co-metathesis of ethylene and olefinic compounds in ionic liquids." Mendeleev Communications 21, no. 6 (November 2011): 329–30. http://dx.doi.org/10.1016/j.mencom.2011.11.012.

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13

Frech, Christian Manfred, Olivier Blacque, and Heinz Berke. "Dinitrosyl rhenium complexes for ring-opening metathesis polymerization (ROMP)." Pure and Applied Chemistry 78, no. 10 (January 1, 2006): 1877–87. http://dx.doi.org/10.1351/pac200678101877.

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The treatment of benzene solutions of the cations [Re(NO)2(PR3)2][BArF4] (R = Cy and R = iPr; [BArF4] = tetrakis{3,5-bis(trifluoromethyl)phenyl}borate) with phenyldiazomethane afforded the moderately stable cationic rhenium(I) benzylidene dinitrosyl bis(trialkyl) phosphine complexes as [BArF4]- salts in good yields. The cationic rhenium dinitrosyl bisphosphine complexes catalyze the ring-opening metathesis polymerization (ROMP) of highly strained nonfunctionalized cyclic olefins to give polymers with relatively high polydispersity indices, high molecular weights, and Z configurations of the double bonds in the polymer chain backbones of over 80 %. The benzylidene derivatives are almost inactive in ROMP catalysis with norbornene and in olefin metathesis. NMR experiments gave first hints for the initial formation of carbene complexes when [Re(NO)2(PR3)2][BArF4] was treated with norbornene. The carbene formation is initiated by an unique reaction sequence where the cleavage of the strained olefinic bond starts with phosphine migration forming a cyclic ylid carbene complex. The [2+2] addition of a norbornene molecule to the Re=C bond leads to the rhenacyclobutane complex, which is expected to be converted into an iminate complex by attack of the ylid function onto one of the NNO atoms followed by Wittig-type phosphine oxide elimination. The formation of phosphine oxide was confirmed by NMR spectroscopy. This species is thought to drive the ROMP metathesis with alternating rhenacyclobutane formations and cycloreversions. The proposed mechanism is supported by density functional theory (DFT) calculations.

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14

Iyer, Karthik, and Jon D. Rainier. "Olefinic Ester and Diene Ring-Closing Metathesis Using a Reduced Titanium Alkylidene." Journal of the American Chemical Society 129, no. 42 (October 2007): 12604–5. http://dx.doi.org/10.1021/ja073880r.

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15

Chang, Sukbok, and Robert H. Grubbs. "A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis." Tetrahedron Letters 38, no. 27 (July 1997): 4757–60. http://dx.doi.org/10.1016/s0040-4039(97)01031-9.

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16

Pollini, Jacqueline, Valentina Bragoni, and Lukas J. Gooßen. "Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid." Beilstein Journal of Organic Chemistry 14 (October 31, 2018): 2737–44. http://dx.doi.org/10.3762/bjoc.14.252.

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A convenient and sustainable three-step synthesis of the tyrosinase inhibitor 2-hydroxy-6-tridecylbenzoic acid was developed that starts directly from the anacardic acid component of natural cashew nutshell liquid (CNSL). Natural CNSL contains 60–70% of anacardic acid as a mixture of several double bond isomers. The anacardic acid component was converted into a uniform starting material by ethenolysis of the entire mixture and subsequent selective precipitation of 6-(ω-nonenyl)salicylic acid from cold pentane. The olefinic side chain of this intermediate was elongated by its cross-metathesis with 1-hexene using a first generation Hoveyda–Grubbs catalyst, which was reused as precatalyst in a subsequent hydrogenation step. Overall, the target compound was obtained in an overall yield of 61% based on the unsaturated anacardic acid content and 34% based on the crude CNSL.

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17

Nuyken, O., K. Karlou-Eyrisch, J. Weis, B. Deubzer, and C. Herzig. "ChemInform Abstract: Synthesis of New α,ω-Olefinic Silicon-Containing Compounds via Cross-Metathesis." ChemInform 31, no. 47 (November 21, 2000): no. http://dx.doi.org/10.1002/chin.200047272.

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18

CHANG, S., and R. H. GRUBBS. "ChemInform Abstract: A Simple Method to Polyhydroxylated Olefinic Molecules Using Ring- Closing Olefin Metathesis." ChemInform 28, no. 41 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199741217.

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19

Blackwell, Helen E., Jack D. Sadowsky, Rebecca J. Howard, Joshua N. Sampson, Jeffery A. Chao, Wayne E. Steinmetz, Daniel J. O'Leary, and Robert H. Grubbs. "Ring-Closing Metathesis of Olefinic Peptides: Design, Synthesis, and Structural Characterization of Macrocyclic Helical Peptides." Journal of Organic Chemistry 66, no. 16 (August 2001): 5291–302. http://dx.doi.org/10.1021/jo015533k.

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20

Ibrahim, Yehia A., Haider Behbehani, Maher R. Ibrahim, and Nada M. Abrar. "Efficient highly stereoselective synthesis of olefinic macrocyclic crown-formazans with the Z-configuration via ring-closure metathesis." Tetrahedron Letters 43, no. 39 (September 2002): 6971–74. http://dx.doi.org/10.1016/s0040-4039(02)01598-8.

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21

Blackwell, Helen E., Jack D. Sadowsky, Rebecca J. Howard, Joshua N. Sampson, Jeffery A. Chao, Wayne E. Steinmetz, Daniel J. O'Leary, and Robert H. Grubbs. "ChemInform Abstract: Ring-Closing Metathesis of Olefinic Peptides: Design, Synthesis, and Structural Characterization of Macrocyclic Helical Peptides." ChemInform 32, no. 46 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200146206.

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22

Zhang, Yuan, and Jon D. Rainier. "Two-Directional Olefinic-Ester Ring-Closing Metathesis using Reduced Ti Alkylidenes. A Rapid Entry into Polycyclic Ether Skeletons." Organic Letters 11, no. 1 (January 2009): 237–39. http://dx.doi.org/10.1021/ol8025439.

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23

Lee, Hyo Won, Sue Hye Yoon, Ihl-Young Choi Lee, and Bong Yong Chung. "ChemInform Abstract: Synthesis of 3,6-Dihydro-2H-pyran Subunits of Laulimalide Using Olefinic Ring Closing Metathesis. Part 2." ChemInform 33, no. 28 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200228164.

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24

Lee, Hyo Won, Chung-Sik Jeong, Sue Hye Yoon, and Ihl-Young Choi Lee. "ChemInform Abstract: Synthesis of 3,6-Dihydro-2H-pyran Subunits of Laulimalide Using Olefinic Ring Closing Metathesis. Part 1." ChemInform 33, no. 16 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200216222.

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25

Nicolaou, K. C., Maarten H. D. Postema, and Christopher F. Claiborne. "Olefin Metathesis in Cyclic Ether Formation. Direct Conversion of Olefinic Esters to Cyclic Enol Ethers with Tebbe-Type Reagents." Journal of the American Chemical Society 118, no. 6 (January 1996): 1565–66. http://dx.doi.org/10.1021/ja9534866.

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26

Rao, H. Surya Prakash, Shaik Rafi, P. Ratish Kumar, C. Guravaiah, and Nandurka Muthanna. "On the stereochemistry of the olefinic double bond in 13-membered heterocyclic rings accessible by ring-closing metathesis reaction." Tetrahedron Letters 53, no. 51 (December 2012): 6877–80. http://dx.doi.org/10.1016/j.tetlet.2012.09.065.

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27

Maier, Martin, and Jochen Neumaier. "Synthesis of the Spirofungin A Core via a Domino Strategy Consisting of Olefinic Ester Ring-Closing Metathesis and Iodospiroacetalization." Synlett 2011, no. 02 (December 23, 2010): 187–90. http://dx.doi.org/10.1055/s-0030-1259287.

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28

Ibrahim, Yehia A., Haider Behbehani, Maher R. Ibrahim, and Nada M. Abrar. "ChemInform Abstract: Efficient Highly Stereoselective Synthesis of Olefinic Macrocyclic Crown-Formazans with the Z-Configuration via Ring-Closure Metathesis." ChemInform 33, no. 50 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200250134.

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29

Rao, H. Surya Prakash, Shaik Rafi, P. Ratish Kumar, C. Guravaiah, and Nandurka Muthanna. "ChemInform Abstract: Stereochemistry of the Olefinic Double Bond in 13-Membered Heterocyclic Rings Accessible by Ring-Closing Metathesis Reaction." ChemInform 44, no. 15 (March 25, 2013): no. http://dx.doi.org/10.1002/chin.201315178.

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30

Weigl, Kerstin, Katrin Köhler, Sebastian Dechert, and Franc Meyer. "Synthesis and Structure of N-Heterocyclic Carbene Complexes with Tethered Olefinic Groups: Application of the Ruthenium Catalyst in Olefin Metathesis." Organometallics 24, no. 16 (August 2005): 4049–56. http://dx.doi.org/10.1021/om0503242.

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31

NICOLAOU, K. C., M. H. D. POSTEMA, and C. F. CLAIBORNE. "ChemInform Abstract: Olefin Metathesis in Cyclic Ether Formation. Direct Conversion of Olefinic Esters to Cyclic Enol Ethers with Tebbe-Type Reagents." ChemInform 27, no. 24 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199624151.

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32

Mihovilovic, Marko D, Birgit Grötzl, Wolfgang Kandioller, Radka Snajdrova, Adél Muskotál, Dario A Bianchi, and Peter Stanetty. "Facile Synthesis and Ring-Opening Cross Metathesis of Carbo- and Heterocyclic Bicyclo[3.2.1]oct-6-en-3-ones Using Gaseous Olefinic Reaction Partners." Advanced Synthesis & Catalysis 348, no. 4-5 (March 2006): 463–70. http://dx.doi.org/10.1002/adsc.200505375.

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33

Saviano, Michele, Ettore Benedetti, Rosa Maria Vitale, Bernard Kaptein, Quirinus B. Broxterman, Marco Crisma, Fernando Formaggio, and Claudio Toniolo. "X-ray Diffraction Analysis and Conformational Energy Computations of β-Turn and 310-Helical Peptides Based on α-Amino Acids with an Olefinic Side Chain. Implications for Ring-Closing Metathesis." Macromolecules 35, no. 10 (May 2002): 4204–9. http://dx.doi.org/10.1021/ma012043l.

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34

HONG, F. T., and L. A. PAQUETTE. "ChemInform Abstract: Olefin Metathesis in Cyclic Ether Formation. Direct Conversion of Olefinic Esters to Cyclic Enol Ethers with Tebbe-Type Reagents. Copper( I)-Promoted Stille Cross-Coupling of Stannyl Enol Ethers with Enol Triflates: Construction of Co." ChemInform 28, no. 28 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199728228.

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35

Quignard, Francoise, Michel Leconte, and Jean Marie Basset. "Aryloxide ligands in metathesis of olefins and olefinic esters: catalytic behaviour of W(OAr)2Cl4 complexes associated with alkyl-tin or alkyl-lead cocatalysts; alkylation of W(OAr)2Cl4 by SnMe4, Sn(n-Bu)4, Pb(n-Bu)4, MgNp2: synthesis of W(OAr)2Cl2(CHCMe3)(OR2) and W(OAr)2Cl(CHCMe3)(CH2CMe3)(OR2)." Journal of Molecular Catalysis 36, no. 1-2 (July 1986): 13–29. http://dx.doi.org/10.1016/0304-5102(86)85098-2.

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36

Postema, Maarten H. D., and Jared L. Piper. "Cross-Metathesis and Ring-Closing Metathesis of Olefinic Monosaccharides." ChemInform 34, no. 2 (January 14, 2003). http://dx.doi.org/10.1002/chin.200302176.

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37

Araiz-Marquez, Ane, Julia Sanchez-Bodón, Antonio Veloso-Fernandez, Leire Ruiz-Rubio, Isabel Moreno Benítez, and Jose Luis Vilas-Vilela. "Eugenola: polimero jasangarrien biomasatik erauzitako lehengaia." EKAIA Euskal Herriko Unibertsitateko Zientzia eta Teknologia Aldizkaria, October 3, 2022. http://dx.doi.org/10.1387/ekaia.23782.

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LABURPENA: Azken urteotan, gizartearen ingurumenaren kalte kezkak bultzaturik, zientzia komunitatean baliabide berriztagarrien interesa handitu egin da. Izan ere, karbono emisioek eta hauek sortzen dituzten hondakinak lehengai jasangarriagoak bilatzera eraman dute. Hortaz, erregai fosilak lehengai naturaletatik ordezkatzea premiazkoa bihurtu da. Talde aromatikoak eta, bereziki, fenolikoak dituzten monomero naturalak oso desiragarriak dira sortzen dituzten material polimerikoen propietate termiko, kimiko eta mekaniko nabarmenengatik. Lan honen bidez, eugenola deritzon lehengai naturalaren funtzionalitate bikainaz baliatuz garatu diren polimerizazio desberdinak bildu dira. Zentzu horretan, erradikal polimerizazio eta kationikoa, metatesis olefinikoa, polikondentsazioa, ene erreakzioak eta tiol-ene erreakzioak erabiliz, eugenol konposatuan oinarritutako polimeroen sintesia aztertu da.

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38

Andreana, Peter R., Jason S. McLellan, Yongchen Chen, and Peng George Wang. "Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis." ChemInform 34, no. 12 (March 25, 2003). http://dx.doi.org/10.1002/chin.200312179.

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39

Yukio, Hitotsuyanagi, Taka-aki Hinosawa, Yoshie Nakagawa, Sho Ito, Ji-Ean Lee, and Tomoyo Hasuda. "Bridged peptide analog of RA-VII, an antitumor bicyclic hexapeptide." Synlett, October 13, 2022. http://dx.doi.org/10.1055/a-1960-4340.

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A bridged peptide analog of RA-VII was designed, in which the α carbons of residues 1 and 4 were linked by a tetramethylene chain to restrict the conformational freedom of the backbone of the 18-membered cyclopeptide. This peptide analog was synthesized by a ring-closing metathesis reaction of [L-2-allylglycine-1, L-2-allylglycine-4]RA-VII and a subsequent hydrogenation of the resulting olefinic compound. Compared with RA-VII, the analog showed much weaker cytotoxic activity toward human promyelocytic leukemia HL-60 cells and human colon carcinoma HCT-116 cells, which may be accounted for by the difference in the orientation of the Tyr-6 phenyl ring plane between the analog and RA-VII.

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40

Iyer, Karthik, and Jon D. Rainier. "ChemInform Abstract: Olefinic Ester and Diene Ring-Closing Metathesis Using a Reduced Titanium Alkylidene." ChemInform 39, no. 12 (March 18, 2008). http://dx.doi.org/10.1002/chin.200812047.

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41

Zhang, Yuan, and Jon D. Rainier. "ChemInform Abstract: Two-Directional Olefinic-Ester Ring-Closing Metathesis Using Reduced Ti Alkylidenes. A Rapid Entry into Polycyclic Ether Skeletons." ChemInform 40, no. 19 (May 12, 2009). http://dx.doi.org/10.1002/chin.200919131.

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42

Kotha, Sambasivarao, and Ramakrishna Reddy Keesari. "An Intramolecular Cycloetherification of Unactivated Olefinic Substrates Bearing endo‐Alcohol: Access to Diversely Alkylated Oxa‐Cage Derivatives Useful for Olefin‐Metathesis." Chemistry – An Asian Journal, October 24, 2022. http://dx.doi.org/10.1002/asia.202200848.

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