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The kinetically controlled iodoetherification reaction of ethyl (S,E)-4,6-dihydroxy-2-hexenoate (1) gives the synthetically useful synthon 2, in which two new stereogenic centers have been generated, with selectivities up to 11:1.The mechanism of this allylic asymmetry transfer was probed by changing the allylic stereogenic substitutent, and the order of efficacy for asymmetric induction was found to be F>OH>/=OMe>Me.This result ruled out several proposed mechanisms of asymmetry transfer and led to the proposal of a transition-structure model, based on AM1 calculations.Our model rationalizes all of our results as well as those from the literature concerning selectivity and even relative rates of diastereomeric substrates.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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(FORMULA PRESENTED) Five-to seven-membered lactones were prepared from omega-hydroxyalkyl iodides and CO by atom transfer carbonylation without the need for transition metal catalysts. The reaction proceeds via a hybrid radical/ionic mechanism in which the intramolecular alcoholysis of an omega-hydroxyacyl iodide, arising from atom transfer carbonylation, leads to the lactone.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Each of a series of C5H8O2 isomeric carboxylic acids and lactones (1-9) was protonated in both concentrated sulfuric acid and trifluoromethanesulfonic acid.The thermally induced transformations of the protonated species were then studied over the temperature range -40 to +160 deg C.As a general rule, all the initially generated cations were eventually converted to protonated gamma-valerolactone (1HO+) and, finally, to protonated cyclopentenone (10HO+).The cations derived from the cyclopropanecarboxylic acids 7 and 8 both underwent ring opening to the unsaturated cation 6HO+, which then rearranged to a protonated alpha-lactone.In concentrated sulfuric acid the latter species loses carbon monoxide to afford protonated 2-butanone 11HO+.The CIMS spectra of compounds 1-9 were recorded, allowing a correlation between the fragmentation routes in the gas phase and the transformations observed in solution.In this way, the data obtained in strong acids are used to assign reasonable structures to the gas-phase ions.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A novel nitrogen-centered tridentate ligand was identified from a series of multidentate ligands and applied for the direct hydrogenation of 9 biogenic acids into alcohols, lactones and esters with high yields. Comparison of substrates and ruthenium precursors suggested that the RuII hydride cationic species was more active to transform acids than the corresponding lactone or esters.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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The asymmetric hydroxylation of the enolates of fully substituted acyclic ester 8 and lactone 10 with (camphorylsulfonyl)oxaziridines 1a – c was studied.The stereoselectivities of the tertiary alpha-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions.While high diastereoselectivity (up to 94percent) was obtained for enolates of fully substituted menthol ester 8 with substoichiometric amounts of oxaziridine 1a, the yields were unsatisfactory.On the other hand, the enantioselective alpha-hydroxylation of the sodium enolate of 2-methyl-gamma-butyrolactone (10) with <(8,8-dimethoxycamphoryl)sulfonyl>oxaziridine (1c) afforded alpha-hydroxy lactone 11a in 70percent yield and 84percent ee.The enantiomeric excess was improved to >93percent ee by crystallization of the corresponding benzoyl ester 11c.The utility of both enantiomers of 11c were demonstrated in the formal asymmetric syntheses of the pheromone, (1S,5R)-(-)-frontalin (13) and in the asymmetric synthesis of (R)-(-)-mevalonolactone (20).

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Novel pyrrolidine alkaloids were isolated from the poison glands of ants Leptothoracini (Myrmicinae) and identified as a mixture of N-alkylated 3-methylpyrrolidines. The females of these species produce male-attracting pheromones in their poison glands. The basic compounds in the secretions were found to be active. The major alkaloid, 3-methyl-1-(3-methylbutyl)pyrrolidine (5), is present in only ng quantities per gland.

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Reference:
Tetrahydrofuran – Wikipedia,
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Intercalates of vanadyl phosphate with alpha-methyl-gamma-butyrolactone, gamma-valerolactone, gamma-caprolactone, delta-valerolactone, and epsilon{lunate}-caprolactone were prepared by a displacement reaction of ethanol-intercalated VOPO4. As follows from the results of elemental analyses and thermogravimetry, intercalates contain about one molecule of the guest per formula unit. The diffractograms of the intercalates show a series of sharp (001) reflections, (200) reflection and some (hkl) lines with low intensity. The tetragonal lattice parameters of the intercalates were calculated. Both delta-valerolactone and epsilon{lunate}-caprolactone intercalates are stable in air. The intercalates of lactones with side aliphatic chains are less stable. The C{double bond, short}O stretching vibration in IR spectra of the intercalates prepared was shifted to lower wavenumbers in comparison with spectra of the pure guests, indicating that lactones are anchored to the host layers by their carbonyl oxygen. Analogously to the arrangement of gamma-butyrolactone, also arrangement of molecules of other lactones in the interlayer space of the host layers was proposed.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Medium-ring lactones react cleanly with primary and secondary aliphatic or aromatic amines in the presence of aluminium chloride at room temperature to afford omega-hydroxyalkylamides in high yield.

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Tetrahydrofuran – Wikipedia,
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A series of 3,3a-dihydro-2H,9H-isoxazolo[3,2-b]-[1,3]benzoxazin 9-ones was synthesized and evaluated for anti-inflammatory, antipyretic and analgesic activity. Since many of these compounds exhibited promising activity, particularly in the anti-inflammatory tests, a number of homologous 2,3,4,4a-tetrahydro-10H-1,2-oxazino[3,2-b]-[1,3]benzoxazin 10-ones and one 3,4,5,5a-tetrahydro-2H, 11H-1,2-oxazepino [3,2-b] [1,3]benzoxazin-11-one, the 9-chloro analog, were also prepared and evaluated. The expanded ring members were generally less active than the tricyclic compounds containing the isoxazolidine rng.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem