109431-72-3Relevant academic research and scientific papers
Cobalt Catalysed Allylic and Benzylic Oxidations with Dioxygen in the Presence of Ethyl 2-oxocyclopentanecarboxylate
Punniyamurthy, T.,Iqbal, Javed
, p. 4003 - 4006 (1994)
An efficient allylic and benzylic oxidation of various cyclic alkenes and benzylic compounds respectively can be achieved with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate 2 and catalytic amount of cobalt(II) Schiff's base complex 1.
Synthesis of C-5'-nor-dideoxycarbanucleosides structurally related to neplanocin C
Comin, Maria J.,Pujol, Carlos A.,Damonte, Elsa B.,Rodriguez, Juan B.
, p. 2219 - 2231 (1999)
Purine carbanucleosides built on a 6-oxabicyclo[3.1.0]hexane template were synthesized from readily available 2-cyclopentenone employing a Mitsunobu reaction to incorporate the base onto the carbocyclic ring. Both adenosine and guanosine analogues exhibited moderate antiviral activity.
SUBSTRATE SPECIFITY IN THE BIOSYNTHESIS OF CYCLOPENTANOID CYANOHYDRIN GLUCOSIDES
Olafsdottir, Elin S.,Joergensen, Lise Bolt,Jaroszewski, Jerzy W.
, p. 4129 - 4134 (1992)
The biosynthesis of deidaclin in Turnera angustifolia and of linamarin in Passiflora morifolia were investigated using intact plant tissues.Radiolabelled precursors, 2-(2'-cyclopentenyl)glycine and L--valine were fed to freshly harvested shoots either alone or together with the presumed nitrile intermediates, 2-cyclopentenecarbonitrile and 2-methylpropanenitrile.The cyanohydrin glucosides were isolated and purified, and the incorporation of the radioactive labels was determined after enzymatic degradation of the glucosides to cyanide.The labels from the amino acid precursors were incorporated into the nitrile group of their corresponding cyanohydrin glucosides, and the incorporation was in each case strongly inhibited by simultaneous feeding with either of the two nitriles.Turnera angustifolia was able to synthesize linamarin when fed with 2-methylpropanenitrile, even though linamarin could not be demonstrated to be present in this plant naturally. Key Word Index - Passiflora morifolia; Passifloraceae; Turnera angustifolia; Turneraceae; cyanohydrin glucosides; radiolabelling; deidaclin; tetraphyllin A; linamarin; lotaustralin; epilotaustralin; 2-(2'-cyclopentenyl)glycine; 2-cyclopentenecarbonitrile; 2-methylpropanenitrile.
Hydroxyl-directed nitrile oxide cycloaddition reactions with cyclic allylic alcohols
Becker, Nina,Carreira, Erick M.
, p. 3857 - 3858 (2007)
Diastereoselective cycloaddition reactions between a nitrile oxide and cyclic allylic alcohols are reported. The products isolated are densely functionalized building blocks that are not otherwise easily accessed with existing methods and concepts previously established for the construction of acyclic polyketides.
Liquid-phase epoxidation of alkenes using molecular oxygen catalyzed by vanadium cation-exchanged montmorillonite
Mitsudome, Takato,Nosaka, Naoya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 1626 - 1627 (2005)
Vanadium cation-exchanged montmorillonite can efficiently catalyze the selective epoxidation of various alkenes and the oxygenation of adamantane using molecular oxygen as a sole oxidant. Copyright
Aerobic oxidation of cycloalkenes catalyzed by iron metal organic framework containing N-hydroxyphthalimide
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
, p. 259 - 265 (2012)
Iron metal organic framework [Fe(BTC)] loaded with N-hydroxyphthalimide (NHPI) promotes the aerobic oxidation of (cyclo)alkenes to give variable percentages of allylic oxidation products and the corresponding epoxide, dependidng on the nature of the substrate. In the case of cyclopentene and cyclohexene, aerobic oxidation catalyzed by NHPI/Fe(BTC) renders their corresponding unsaturated cyclic alcohol and ketone with 97% selectivity in 5 h at 6% and 12% conversion, respectively. Under the same experimental conditions, cyclooctene exhibited 95% selectivity toward the formation of cyclooctene oxide with 2% of cyclooctenol/one at 4 h. Cycloheptene as susbstrate exhibits an intermediate behavior, and the aerobic oxidation catalyzed by NHPI/Fe(BTC) leads to the formation of cycloheptenol/cycloheptenone with 77% selectivity, accompanied by 23% of cycloheptene oxide at 4 h. Further experiments with non-symmetric olefins exhibited also a mixture of products including epoxides and allyic products. A mechanism to explain these experimental results has been proposed.
Facile isomerization of oxiranes to allyl alcohols by mixed metal bases
Mordini, Alessandro,Rayana, Ezzedine Ben,Margot, Christian,Schlosser, Manfred
, p. 2401 - 2410 (1990)
The mixture of lithium diisopropylamide and potassium tert-butoxide ("LIDAKOR reagent") promotes smooth ring opening of oxiranes to afford allyl alcohols with good to excellent yields. Internal epoxyalkanes and large size epoxy-cycloalkanes give preferentially or exclusively trans-alkenols. The regio- and stereochemistry of the ring opening reaction are essentially the consequence of syn-periplanar elimination mechanisms.
Reductive alkylation of β-alkoxy aziridines: New route to substituted allylic amines
Rosser, Clare M.,Coole, Susannah C.,Kirby, Jonathan P.,O'Brien, Peter,Caine, Darren
, p. 4817 - 4819 (2004)
(Chemical Equation Presented) A new route to substituted cyclic allylic amines via the reductive alkylation of β-alkoxy aziridines using excess alkyllithium reagents is described.
Asymmetric Catalysis by Vitamin B12. The Mechanism of the Cob(I)alamin-Catalyzed Isomerization of 1,2-Epoxycyclopentane to (R)-Cyclopent-2-enol
Bonhote, Pierre,Scheffold, Rolf
, p. 1425 - 1444 (1991)
The isomerization of 1,2-epoxycyclopentane (1) to enantiomerically enriched (R)-cyclopent-2-enol (2) in protic solvents is catalyzed by cob(I)alamin.The enantiomeric excess (e.e.) of (R)-2 is usually ca. 60percent; it is only slightly dependent on the temperature, but increases with decreasing dielectric constant ε of the solvent.Standard kinetic methods show the reaction to be first order in vitamine B12 and zero order in 1.The rate constant increases exponentially with increasing ε of the solvent.An Arrhenius plot at ε = 40 gives activation parameters ΔH(excit.) = 78 +/- 4 kJ*mol-1 and ΔS(excit.) = -49 +/- 1 J*mol-1*K-1.The isomerization 1 --> 2 proceeds in two steps (Schemes 2 and 7): i) The epoxide ring is first opened by the proton-assisted fast and irreversible nucleophile attack of the chiral CoI catalyst to form diastereomeric (1R,2R)- and (1S,2S)-(2-hydroxycyclopentyl)cob(III)alamins 6 in a ratio of ca. 4:1 which are the dominant species in the steady state; ii) The intermediates 6 then decompose in the rate limiting step to form 2 and recycled catalyst.Experiments with specifically 2H-labeled 1 showed the hydro-cobalt elimination 6 --> 2 to be non-stereoselective.It proceeds via reversible Co-C bond homolysis to a free 2-hydroxycyclopentyl radical from which stereoelectronically controlled H-abstraction by CoII takes place.
Highly active delaminated Ti-MWW for epoxidation of bulky cycloalkenes with hydrogen peroxide
Nuntasri, Duangamol,Wu, Peng,Tatsumi, Takashi
, p. 326 - 327 (2003)
A novel titanosilicate, prepared by the partial delamination of acid-treated Ti-MWW, possesses an extremely high specific surface area and proves to be a selective and active liquid-phase oxidation catalyst for bulky alkenes.
