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Stereoselective Nitroolefination of Active Methine of Various Carbonyl Compounds with beta-Nitroenamines

Enolates of carbonyl compounds having a methine alpha-carbonyl undergo 2-nitro-1-alkenylation (nitroolefination) to form quarternary C-atom next to the carbonyl group on reaction with beta-nitroenamines via an addition elimination process.The geometry of the resulting nitroolefins proved to be of the E type.

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

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Facile synthesis of versatile enantioenriched alpha-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution

An efficient synthesis of enantioenriched alpha-substituted gamma-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Bronsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.

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

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INDANE AND INDOLINE DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

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

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Seven membered ring chelates derived from gamma-hydroxyamides and triphenyltin or diphenylboron

N-Benzyl-4-hydroxy-butyramide (1), 4-hydroxy-N-[(R)-1-phenyl-ethyl]-butyramide (2), and (R)-4-hydroxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (3a) were used to prepare new diphenylboron and triphenyltinoxy compounds: diphenylborinic acid 3-benzylcarbamoyl-propyl ester (4), diphenylborinic acid 3-[(R)-1-phenyl-ethylcarbamoyl]-propyl ester (5) and diphenylborinic acid (R)-3-[(R)-1-phenyl-ethylcarbamoyl]-butyl ester (6), N-benzyl-4-triphenyltinoxy-butyramide (7), 4-triphenyltinoxy-N-[(R)-1-phenyl-ethyl]-butyramide (8), and (R)-4-triphenyltinoxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (9). The X-ray diffraction analysis of a crystalline structure of the new gamma-hydroxyamide 3a is reported, as well as that of the first example of a crystalline structure where a diphenylborinic ester forms a seven membered chelate, by a carbonyl coordination to boron (4). Structural studies of tin and boron esters were performed by NMR. The C{double bond, long}O internal coordination to tin atoms, affording seven membered rings, was observed by 119Sn NMR experiments at low temperature.

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Tetrahydrofuran – Wikipedia,
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Synthesis of Delta1<9>– and/or Delta8<9>-Dehydroindolizidines and Related Compounds

A facile synthesis of Delta1<9>– and/or Delta8<9>-dehydroindolizidine and related compounds, consisting of dry distillation of gamma-(N-2-piperidinonyl)butyric acid over soda-lime, is described.Reductions of these dehydroindolizidines and stereochemistry of 1-methylindolizidine are also described.

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

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An expedient synthesis of olfactory lactones by intramolecular hydroacylalkoxylation reactions

A series of 4,5-disubstituted gamma-lactones, including whisky and cognac lactones, was synthesised in four steps from a readily available chiral precursor. By using an intramolecular hydroacylalkoxylation reaction in the final step, a correlation between the (E)/(Z) configuration of the precursor and the product distribution has been established, for the first time, in this type of cyclisation reactions. Copyright

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Tetrahydrofuran – Wikipedia,
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Syntheses of Hydroxy Ketones from Lactones

gamma-Hydroxy ketones (4, n=2) are cleanly obtained by the addition of 1.1 equiv of n-butyllithium to gamma-lactones dissolved in ether at -90 deg C, since in these conditions the formation of diols by double organometallic attack is avoided, especially in the case of substituted lactones.The corresponding reactions performed in tetrahydrofuran are less satisfactory.The method cannot be applied to delta-valerolactone and epsilon-caprolactone, as well as to beta-lactones, from which extremely complex mixtures are obtained in low yields.Furthermore the reactions of Grignard reagentswith lactones in ether or in tetrahydrofuran are quite poor.From those lactones which behave unsatisfactorily toward n-butyllithium in ether, the corresponding beta-, delta-, and epsilon-hydroxy ketones (4, n=1, 3, 4) are prepared in two steps.The reactions with alpha,alpha-dilithioalkyl phenyl sulfones in tetrahydrofuran at low temperatures afford the omega-hydroxy-beta-keto sulfones (12), which are successively cleaved with aluminum amalgam to afford 4 in satisfactory overall yields.

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Tetrahydrofuran – Wikipedia,
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Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones

The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent beta-radical fragmentation to generate lactones.

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

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Extension of the Eschenmoser sulfide contraction/iminoester cyclization method to the synthesis of tolyporphin chromophore

Tolyporphin chromophore 2 has been synthesized by performing a double-retroaldol/oxidation sequence on an octahydroporphyrin precursor 18 prepared by using the Eschenmoser sulfide-contraction/iminoester-condensation method.

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Tetrahydrofuran – Wikipedia,
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N,S-Dimethyldithiocarbamyl oxalates (e.g.6, 10) are novel, readily prepared precursors to alkyloxyacyl radicals 1 that are more suitable for kinetic studies than existing precursors; 10 has allowed the determination of accurate rate data for the cyclization of the butenyloxyacyl radical 5 (kc = 1.2 × 107 s-1 at 21 C). This journal is

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