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Journal articles on the topic 'Acyclic epoxidation'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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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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2

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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11

Sun, Bing-Feng, Ran Hong, Yan-Biao Kang, and Li Deng. "Asymmetric Total Synthesis of (−)-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstitued Olefins." Journal of the American Chemical Society 131, no. 30 (August 5, 2009): 10384–85. http://dx.doi.org/10.1021/ja9039407.

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12

Freccero, Mauro, Remo Gandolfi, Mirko Sarzi-Amadè, and Augusto Rastelli. "Epoxidation of Acyclic Chiral Allylic Alcohols with Peroxy Acids: Spiro or Planar Butterfly Transition Structures? A Computational DFT Answer." Journal of Organic Chemistry 65, no. 7 (April 2000): 2030–42. http://dx.doi.org/10.1021/jo991530k.

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13

NAGATA, T., K. IMAGAWA, T. YAMADA, and T. MUKAIYAMA. "ChemInform Abstract: Enantioselective Aerobic Epoxidation of Acyclic Simple Olefins Catalyzed by the Optically Active β-Ketoiminato Manganese(III) Complex." ChemInform 26, no. 1 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199501133.

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14

Wu, Shaoxiang, Dong Pan, Chengyao Cao, Qi Wang, and Fu-Xue Chen. "Diastereoselective and Enantioselective Epoxidation of Acyclic β-Trifluoromethyl-β,β-Disubstituted Enones by Hydrogen Peroxide with a Pentafluorinated Quinidine-Derived Phase-Transfer Catalyst." Advanced Synthesis & Catalysis 355, no. 10 (July 8, 2013): 1917–23. http://dx.doi.org/10.1002/adsc.201300249.

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15

Wu, Shaoxiang, Dong Pan, Chengyao Cao, Qi Wang, and Fu-Xue Chen. "ChemInform Abstract: Diastereoselective and Enantioselective Epoxidation of Acyclic β-Trifluoromethyl-β,β-Disubstituted Enones by Hydrogen Peroxide with a Pentafluorinated Quinidine-Derived Phase-Transfer Catalyst." ChemInform 44, no. 51 (December 2, 2013): no. http://dx.doi.org/10.1002/chin.201351118.

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16

Adam, Waldemar, Catherine M. Mitchell, and Chantu R. Saha-Möller. "Regio- and Diastereoselective Catalytic Epoxidation of Acyclic Allylic Alcohols with Methyltrioxorhenium: A Mechanistic Comparison with Metal (Peroxy and Peroxo Complexes) and Nonmetal (Peracids and Dioxirane) Oxidants." Journal of Organic Chemistry 64, no. 10 (May 1999): 3699–707. http://dx.doi.org/10.1021/jo9902289.

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17

Adam, Waldemar, Catherine M. Mitchell, and Chantu R. Saha-Moeller. "ChemInform Abstract: Regio- and Diastereoselective Catalytic Epoxidation of Acyclic Allylic Alcohols with Methyltrioxorhenium: A Mechanistic Comparison with Metal (Peroxy and Peroxo Complexes) and Nonmetal (Peracids and Dioxirane) Oxidants." ChemInform 30, no. 35 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199935060.

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18

Taylor, Richard J., Julie C. McManus, and John S. Carey. "Enantiopure Guanidine Bases For Enantioselective Enone Epoxidations: 1, Acyclic Guanidines." Synlett, no. 3 (2003): 0365–68. http://dx.doi.org/10.1055/s-2003-37105.

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19

Adam, Waldemar, Hans-Günter Brünker, A. Sampath Kumar, Eva-Maria Peters, Karl Peters, Uwe Schneider, and Hans Georg von Schnering. "Diastereoselective Singlet Oxygen Ene Reaction (Schenck Reaction) and Diastereoselective Epoxidations of Heteroatom-Substituted Acyclic Chiral Olefins: A Mechanistic Comparison." Journal of the American Chemical Society 118, no. 8 (January 1996): 1899–905. http://dx.doi.org/10.1021/ja9530230.

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20

Roush, William R., Julie A. Straub, and Richard J. Brown. "Total synthesis of carbohydrates. 5. Stereochemistry of the epoxidations of acyclic allylic amides. Applications towards the synthesis of 2,3,6-trideoxy-3-aminohexoses." Journal of Organic Chemistry 52, no. 23 (November 1987): 5127–36. http://dx.doi.org/10.1021/jo00232a014.

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21

Adam, Waldemar, and Alexander K. Smerz. "Solvent Effects in the Regio- and Diastereoselective Epoxidations of Acyclic Allylic Alcohols by Dimethyldioxirane: Hydrogen Bonding as Evidence for a Dipolar Transition State." Journal of Organic Chemistry 61, no. 10 (January 1996): 3506–10. http://dx.doi.org/10.1021/jo951984r.

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22

"Asymmetric Nucleophilic Epoxidation of Acyclic Trisubstituted Olefins." Synfacts 2009, no. 10 (September 22, 2009): 1125. http://dx.doi.org/10.1055/s-0029-1217852.

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23

Shin, Bongki, Shinji Tanaka, Tetsuya Kita, Yuichi Hashimoto, and Kazuno Nagasawa. "ChemInform Abstract: Development of Bifunctional Acyclic Hydroxyl-guanidine Organocatalyst: Application to Asymmetric Nucleophilic Epoxidation." ChemInform 40, no. 11 (March 17, 2009). http://dx.doi.org/10.1002/chin.200911112.

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24

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." ChemInform 36, no. 28 (July 12, 2005). http://dx.doi.org/10.1002/chin.200528111.

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25

Sun, Bing-Feng, Ran Hong, Yan-Biao Kang, and Li Deng. "ChemInform Abstract: Asymmetric Total Synthesis of (-)-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstituted Olefins." ChemInform 41, no. 2 (January 12, 2010). http://dx.doi.org/10.1002/chin.201002111.

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26

Tang, Yu, J. Brent Friesen, Dejan S. Nikolić, David C. Lankin, James B. McAlpine, Shao-Nong Chen, and Guido F. Pauli. "Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts." Planta Medica, May 11, 2021. http://dx.doi.org/10.1055/a-1472-6164.

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AbstractPrenyl moieties are commonly encountered in the natural products of terpenoid and mixed biosynthetic origin. The reactivity of unsaturated prenyl motifs is less recognized and shown here to affect the acyclic Rhodiola rosea monoterpene glycoside, kenposide A (8), which oxidizes readily on silica gel when exposed to air. The major degradation product mediated under these conditions was a new aldehyde, 9. Exhibiting a shortened carbon skeleton formed through the breakdown of the terminal isopropenyl group, 9 is prone to acetalization in protic solvents. Further investigation of minor degradation products of both 8 and 8-prenylapigenin (8-PA, 12), a flavonoid with an ortho-prenyl substituent, revealed that the aldehyde formation was likely realized through epoxidation and subsequent cleavage at the prenyl olefinic bond. Employment of 1H NMR full spin analysis (HiFSA) achieved the assignment of all chemical shifts and coupling constants of the investigated terpenoids and facilitated the structural validation of the degradation product, 9. This study indicates that prenylated compounds are generally susceptible to oxidative degradation, particularly in the presence of catalytic mediators, but also under physiological conditions. Such oxidative artifact/metabolite formation leads to a series of compounds with prenyl-derived (cyclic) partial structures that are analogous to species formed during Phase I metabolism in vivo. Phytochemical and pharmacological studies should take precautions or at least consider the impact of (unavoidable) exposure of prenyl-containing compounds to catalytic and/or oxidative conditions.

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27

McManus, Julie C., John S. Carey, and Richard J. K. Taylor. "Enantiopure Guanidine Bases for Enantioselective Enone Epoxidations. Part 1. Acyclic Guanidines." ChemInform 34, no. 23 (June 10, 2003). http://dx.doi.org/10.1002/chin.200323088.

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28

ROUSH, W. R., J. A. STRAUB, and R. J. BROWN. "ChemInform Abstract: Stereochemistry of the Epoxidations of Acyclic Allylic Amides. Applications toward the Synthesis of 2,3,6-Trideoxy-3-aminohexoses." ChemInform 19, no. 17 (April 26, 1988). http://dx.doi.org/10.1002/chin.198817158.

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