14519-31-4Relevant articles and documents
Total synthesis of the naturally occurring furanoid fatty acid, F5
Marson, Charles M.,Harper, Steven
, p. 333 - 334 (1998)
The furanoid fatty acid F5 has been synthesized using a mercury(II) catalyzed isomerization of 2-(1,2-oxiranylcyclododecyl)-3-nonyn-2-ol.
Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones
Beller, Matthias,Ge, Yao,Jackstell, Ralf,Jiao, Haijun,Liu, Jiawang,Spannenberg, Anke,Yang, Ji,Ye, Fei
supporting information, p. 21585 - 21590 (2020/09/23)
The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.
Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives
Gronnier, Colombe,Boissonnat, Guillaume,Gagosz, Fabien
, p. 4234 - 4237 (2013/09/12)
A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.
A novel, short and repeatable two-carbon ring expansion reaction by thermo-isomerization: Easy synthesis of macrocyclic ketones
Nagel, Matthias,Hansen, Hans-Ju?rgen,Fra?ter, Georg
, p. 275 - 279 (2007/10/03)
A novel two-carbon ring enlargement procedure, in which medium- and large-ring 1-vinylcycloalkanols are thermoisomerized in a flow reactor system at temperatures of 600°C to about 650°C, produces the isomeric ring-expanded cycloalkanones directly and efficiently. This two-step ring expansion protocol can easily be applied several times successively. For e.g., the musk odorant cyclopentadecanone (Exaltone?) is prepared from cycloundecanone in two repetitive cycles. Thermo-isomerization of the corresponding ethynylic cycloalkanols gives in moderate yields the bishomologous α,β-unsaturated macrocyclic (E)-2-cycloalkenones. A reaction mechanism via alkyl hydroxyallyl biradical intermediates is proposed.
Highly stereoselective synthesis of bicyclo[n.3.0]alkanes by titanium tetrachloride promoted [3 + 2] cycloaddition of allylsilanes and 1-acetylcycloalkenes
Knoelker, Hans-Joachim,Foitzik, Norbert,Goesmann, Helmut,Graf, Regina,Jones, Peter G.,Wanzl, Guenter
, p. 538 - 551 (2007/10/03)
The titanium tetrachloride promoted reaction of allylsilanes 1 with 1-acetylcyclohexene is shown to afford the silylbicyclo[4.3.0]nonanes 9 ([3 + 2] cycloaddition products) along with the 1-acetyl-2-allylcyclohexane 4 (Hosomi-Sakurai product). Here we report that systematic variation of the substituents at the silicon atom of 1 allows suppression of the classical Hosomi Sakurai reaction in favor of the [3+2] cycloaddition. Cycloaddition of the allylsilanes 1d, 1i, and 1k with 1-acetylcycloalkenes 10, containing a 5-, 6-, 7-, 8-, or 12-membered ring, gives rise to the corresponding silylbicyclo[n.3.0]alkanes 11-13. The cycloaddition of allyltriisopropylsilane (1k) and 1-acetyl-2-methylcycloalkenes 15 provides silylbicyclo[n.3.0]alkanes 16 with two contiguous quaternary carbon centers. The stereochemistry of the silylbicyclo[n.3.0]alkanes 11a-c and 14 is unambiguously determined by X-ray analysis and 13C NMR spectroscopy.
SYNTHESIS OF 1-ETHYNYLCYCLODODECANOL AND ITS ISOMERIZATION AT A VANADIUM CATALYST
Zakharkin, L. I.,Pryanishnikov, A. P.,Ovseenko, S. T.
, p. 699 - 701 (2007/10/02)
A simple procedure was developed for the production of 1-ethynylcyclododecanol by the condensation of acetylene with cyclododecanone by the action of potassium hydroxide in solvating solvents at atmospheric pressure.The isomerization of 1-ethynylcyclododecanol at homogeneous vanadium catalysts gave an equilibrium mixture of cyclododecylideneethanal and cyclododecenylethanal, of which the latter exists in the form of a mixture of cis and trans isomers.
SYNTHESIS OF 1-(3-HYDROXYPROPYNYL)-1-CYCLODODECANOL AND ITS CYCLIZATION TO BICYCLOPENTADEC-1(12)-EN-13-ONE
Zakharkin, L. I.,Pryanishnikov, A. P.,Guseva, V. V.
, p. 83 - 85 (2007/10/02)
Methods were developed for the synthesis of 1-(3-hydroxypropynyl)-1-cyclododecanol from cyclododecanone and propargyl alcohol and from 1-ethynyl-1-cyclododecanol and formaldehyde.Its cyclization to bicyclopentadec-1(12)-en-13-one was investigated.
