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Relevant bibliographies by topics / Acyclic epoxidation

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Academic literature on the topic 'Acyclic epoxidation'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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Journal articles on the topic "Acyclic epoxidation"

1

Kurihara, Masaaki, Kei Ishii, Yoko Kasahara, Mari Kameda, Ashish K. Pathak, and Naoki Miyata. "Stereoselective Epoxidation of Acyclic Allylic Ethers Using Ketone-Oxone®System." Chemistry Letters 26, no. 10 (October 1997): 1015–16. http://dx.doi.org/10.1246/cl.1997.1015.

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Dias, Lucas D., Rui M. B. Carrilho, César A. Henriques, Giusi Piccirillo, Auguste Fernandes, Liane M. Rossi, M. Filipa Ribeiro, Mário J. F. Calvete, and Mariette M. Pereira. "A recyclable hybrid manganese(III) porphyrin magnetic catalyst for selective olefin epoxidation using molecular oxygen." Journal of Porphyrins and Phthalocyanines 22, no. 04 (April 2018): 331–41. http://dx.doi.org/10.1142/s108842461850027x.

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The synthesis and characterization of a hybrid Mn(III)-porphyrin magnetic nanocomposite is described. Moreover, a sustainable methodology for epoxidation of olefins is reported, using O[Formula: see text] as a green oxidant and the magnetic nanoparticle as a recyclable catalyst. High activity in alkene oxidation was observed, with full selectivity for epoxide formation. The magnetic catalyst presented high stability, being recovered and reused in five consecutive runs without loss of catalytic activity or selectivity in cyclooctene oxidation. Moreover, the catalytic system showed very good reactivity toward epoxidation of a range of terminal, substituted, cyclic or acyclic, aliphatic and aromatic olefins, including terpene and steroid derivatives, affording a range of biologically relevant epoxides in excellent yields. The isobutyric acid, formed as side-product, was recovered with high yield and purity, which provides the potential reutilization of this important industrial product.

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3

Sirimanne, S. R., and S. W. May. "Interaction of non-conjugated olefinic substrate analogues with dopamine β-monooxygenase: catalysis and mechanism-based inhibition." Biochemical Journal 306, no. 1 (February 15, 1995): 77–85. http://dx.doi.org/10.1042/bj3060077.

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The reaction of dopamine beta-monooxygenase (DBM; EC 1.14.17.1) with the prototypical non-conjugated olefinic substrate, 2-(1-cyclohexenyl)ethylamine (CyHEA) [see Sirimanne and May (1988) J. Am. Chem. Soc. 110, 7560-7561], was characterized. CyHEA undergoes facile DBM-catalysed allylic hydroxylation to form (R)-2-amino-1-(1-cyclohexenyl)ethanol (CyHEA-OH) without detectable epoxidation or allylic hydroxylation to form (R)-2-amino-1-(1-cyclohexenyl)ethanol (CyHEA-OH) without detectable epoxidation or allylic rearrangement, and with stereochemistry consistent with that of DBM-catalysed benzylic hydroxylation and sulphoxidation. The kcat. of 90 s-1 for CyHEA oxygenation is about 75% of the kcat. for tyramine, the substrate commonly used in assays of DBM activity. DBM-catalysed oxygenation of CyHEA also results in mechanism-based inactivation of DBM, with the inactivation reaction yielding kinact. = 0.3 min-1 at pH 5.0 and 37 degrees C, and a partition ratio of 16,000. Although both CyHEA turnover and inactivation exhibit normal kinetics, CyHEA processing also results in gradual depletion of copper from DBM; however, mechanism-based irreversible DBM inactivation occurs independent of this copper depletion when sufficient copper is present in the assay solution. A likely mechanism for turnover-dependent DBM inactivation by CyHEA involves initial abstraction of an allylic hydrogen to form a resonance-stabilized allylic radical, which can then either partition to product or undergo attack by an active-site residue. Acyclic, non-conjugated olefinic analogues exhibit diminished substrate activity toward DBM. Thus, kcat. for oxygenation of cis-2-hexenylamine, which also produces only allylic alcohol product, is only 14% of that for CyHEA. Similarly, kinact./KI for turnover-dependent inactivation by the acyclic olefin 2-aminomethyl-1-pentene is more than an order of magnitude smaller than that for benzylic olefins. Our results establish that DBM catalyses allylic oxygenation of a number of non-conjugated olefinic substrate analogues with neither epoxidation nor allylic rearrangement occurring. The absence of epoxide products from non-conjugated olefinic substrates implies an inability of the activated copper-oxygen species of DBM to effect radical cation formation from a non-conjugated olefinic moiety. The striking contrast between DBM and cytochrome P-450, which carries out both epoxidation and allylic oxidation with non-conjugated olefinic substrates, is probably a reflection of the differences in redox potential of the activated oxygen species operative for these two enzymes.

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4

KURIHARA, M., K. ISHII, Y. KASAHARA, M. KAMEDA, A. K. PATHAK, and N. MIYATA. "ChemInform Abstract: Stereoselective Epoxidation of Acyclic Allylic Ethers Using Ketone-Oxone® System." ChemInform 29, no. 6 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199806141.

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5

Lurain, Alice E., Patrick J. Carroll, and Patrick J. Walsh. "One-Pot Asymmetric Synthesis of Acyclic Chiral Epoxy Alcohols via Tandem Vinylation−Epoxidation with Dioxygen." Journal of Organic Chemistry 70, no. 4 (February 2005): 1262–68. http://dx.doi.org/10.1021/jo048345d.

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6

Maligres, P. E., S. A. Weissman, V. Upadhyay, S. J. Cianciosi, R. A. Reamer, R. M. Purick, J. Sager, et al. "Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides." Tetrahedron 52, no. 9 (February 1996): 3327–38. http://dx.doi.org/10.1016/0040-4020(95)01114-5.

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7

Nagata, Takushi, Kiyomi Imagawa, Tohru Yamada, and Teruaki Mukaiyama. "Enantioselective Aerobic Epoxidation of Acyclic Simple Olefins Catalyzed by the Optically Active β-Ketoiminato Manganese(III) Complex." Chemistry Letters 23, no. 7 (July 1994): 1259–62. http://dx.doi.org/10.1246/cl.1994.1259.

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8

Freccero, Mauro, Remo Gandolfi, Mirko Sarzi-Amadè, and Augusto Rastelli. "Peroxy Acid Epoxidation of Acyclic Allylic Alcohols. Competition between s-trans and s-cis Peroxy Acid Conformers." Journal of Organic Chemistry 70, no. 23 (November 2005): 9573–83. http://dx.doi.org/10.1021/jo0515982.

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9

Rodríguez-Berríos, Raúl R., Gerardo Torres, and José A. Prieto. "Stereoselective VO(acac)2 catalyzed epoxidation of acyclic homoallylic diols. Complementary preparation of C2-syn-3,4-epoxy alcohols." Tetrahedron 67, no. 5 (February 2011): 830–36. http://dx.doi.org/10.1016/j.tet.2010.11.079.

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10

MALIGRES, P. E., S. A. WEISSMAN, V. UPADHYAY, S. J. CIANCIOSI, R. A. REAMER, R. M. PURICK, J. SAGER, et al. "ChemInform Abstract: Cyclic Imidate Salts in Acyclic Stereochemistry: Diastereoselective syn-Epoxidation of 2-Alkyl-4-enamides to Epoxyamides." ChemInform 27, no. 25 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199625044.

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Dissertations / Theses on the topic "Acyclic epoxidation"

1

Bish, E. H. "Aspects of stereochemical control in organic synthesis." Thesis, University of Oxford, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.370238.

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Book chapters on the topic "Acyclic epoxidation"

1

Singh, R. P., and L. Deng. "Epoxidation of Acyclic Enones." In Brønsted Base and Acid Catalysts, and Additional Topics, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00102.

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2

"Chapter 10 10. Acyclic stereoselection II: Asymmetric epoxidation and dihydroxylation of olefinic double bonds." In Organic Chemistry in Action - The Design of Organic Synthesis, 277–91. Elsevier, 1996. http://dx.doi.org/10.1016/s0165-3253(96)80016-2.

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3

Taber, Douglass. "The Sammakia Synthesis of the Macrolide RK-397." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0083.

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The polyene macrolide RK-397 3, isolated from soil bacteria, has antifungal, antibacterial and anti-tumor activity. Tarek Sammakia of the University of Colorado has described (Angew. Chem. Int. Ed. 2007, 46, 1066) the highly convergent coupling of 1 with 2, leading to 3. The preparation of 1 depended on the powerful methods that have been developed for acyclic stereocontrol. Beginning with the allylic alcohol 4, Sharpless asymmetric epoxidation established the absolute configuration of 5. Following the Jung “non-aldol aldol” protocol, exposure of 5 to TMSOTf delivered the aldehyde 6 in high de. Condensation of 6 with the lithium enolate of acetone also proceeded with high de. The resulting alcohol was protected as the MOM ether, to direct the stereoselectivity of the subsequent aldol condensation with 8. Selective β-elimination followed by reduction and protecting group exchange then gave 1. The preparation of 2 took advantage of the power of Brown asymmetric allylation. Allylation of the symmetrical 11 led to the diol 12. This was desymmetrized by selective acetonide formation, to give 13. Ozonolysis, reductive work-up, and protection of the newly-formed 1,3-diol gave 14, setting the stage for oxidation and asymmetric allylation to give 15. Reductive deprotection and oxidation then delivered the acetonide 2. The tris acetonide 16 was assembled by addition of the enolate derived from 1 to the aldehyde 2, followed by reduction and protection. Kinetically-controlled metathesis with 17 established the triene 18. Phosphonate-mediated homologation to the pentaene 19 followed by hydrolysis and Yamaguchi macrolactonization then completed the synthesis of the macrolide RK-397 3.

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4

Taber, Douglass F. "Arrays of Stereogenic Centers: The Barker Synthesis of (+)-Galbelgin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0043.

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Gang Zhao of the Shanghai Institute of Organic Chemistry and Gang Zou of the East China University of Science and Technology devised (Adv. Synth. Catal. 2011, 353, 3129) an elegant catalyst for the direct enantioselective epoxidation of a simple acyclic enone 1. Ismail Ibrahem and Armando Córdova of Mid Sweden University and Stockholm University prepared (Adv. Synth. Catal. 2011, 353, 3114) 6 by combining three catalysts to effect the enantioselective addition of 5 to 4. Giovanni Casiraghi and Franca Zanardi of the Università degli Studi di Parma used (J. Org. Chem. 2011, 76, 10291) a silver catalyst to mediate the addition of 8 to 7 to give 9. Keiji Maruoka of Kyoto University condensed (Nature Chem. 2011, 3, 642) the diazo ester 10 with an aldehyde 4, leading, after reduction of the initial adduct and protection, to the diamine 11. Christoph Schneider of the Universität Leipzig effected (Synthesis 2011, 4050) the vinylogous addition of 13 to an imine 12, setting both stereogenic centers of 14. In the course of the coupling of 16 with the diol 15, Michael J. Krische of the University of Texas established (J. Am. Chem. Soc. 2011, 133, 12795) four new stereogenic centers. By adding (Chem. Commun. 2011, 47, 10557) an α-nitro ester 18 to the maleimide 19, Professor Maruoka established both the alkylated secondary center and the N-substituted quaternary center of 20. Srinivas Hotha of the Indian Institute of Science Education & Research and Torsten Linker of the University of Potsdam showed (Chem. Commun. 2011, 47, 10434) that the readily prepared lactone 21 could be opened to 23 without disturbing the stereogenic center adjacent to the carbonyls. Allan D. Headley and Bukuo Ni of Texas A&M University-Commerce devised (Synthesis 2011, 1993) a recyclable catalyst for the addition of an aldehyde 7 to a nitroalkene 24 in water to give 25. Alexandre Alexakis of the University of Geneva effected (Chem. Commun. 2011, 47, 7212) the triply convergent coupling of 26, 27, and 28 to give 29 as a single dominant diastereomer.

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5

Taber, Douglass F. "The Trost Synthesis of (-)-Pseudolaric Acid B." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0085.

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(-)-Pseudolaric acid B 3, isolated from the bark of the golden larch Pseudolarix kaempferi, shows potent antifungal activity. A key step in the total synthesis of 3 described (J. Am. Chem. Soc. 2008 , 130 , 16424) by Barry M. Trost of Stanford University was the free radical cyclization of 1 that established the angular ester and the trans ring fusion of 2 and thus of 3. To prepare the bicyclic skeleton of 1, the authors envisioned the Rh-mediated intramolecular addition of the alkyne of 11 to the alkenyl cyclopropane. The acyclic centers of 11 were established by Noyori hydrogenation of (equilibrating) racemic 4. One enantiomer reduced much more quickly than the other, leading to 5. The absolute configuration of the cyclopropane was set by Charette cyclopropanation of the monosilyl ether of the inexpensive diol 8. The two components were then coupled using a Corey-Schlosser protocol. Alkylation of the ylide 10 with 7 gave a new phosphonium salt, which in situ was deprotonated and condensed with the aldehyde 9 . The resulting betaine was deprotonated and quenched, then exposed again to base to give the trans alkene 11. It is important in this procedure to use PhLi as the base, because the alkyl lithium can displace the alkyl group on phosphorus. The product from Ru-catalyzed cyclization was the expected 1,4-diene 12 . Fortunately, it was found that TBAF desilylation led to concomitant alkene migration, to give the more stable conjugated diene 13. Selective epoxidation of the more electron-rich alkene fol lowed by exposure to strong base then delivered 14 , with the requisite angular oxygenation established. Pseudolaric acid B 3 would be derived from cyclization of the selenocarbonate of a tertiary alcohol. In fact, however, attempted cyclization of such selenocarbonates led only to decarboxyation and reduction. Even with the selenocarbonate 1 prepared from the secondary alcohol, the cyclization to 2 required careful optimization, including using not AIBN but azobis(dicyclohexylcarbonitrile) as the radical initiator. Acetylide addition to the ketone 15 could be effected with high diastereocontrol, but lactone construction proved elusive. Alkaline conditions led quickly to addition of the angular hydroxyl to the activated alkene in the seven-membered ring.

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