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Cyclopropane Derivatives, 2. – Self-Acylation of alpha-Alkyl-gamma-lactones To Give Bis(1-alkylcyclopropyl)ketones via Spiro<4.4>acetals

High-yield synthetic ways are recommended for the title lactones 1.The coupling of two 2-alkyl-4-butanolides is possible in an inter-(1b, c) or intramolecular fashion (4c) to give spiro<4.4>acetals 8 or 9, respectively, in the absence of hindering substituents.Symmetrically substituted bis(1-alkylcyclopropyl)ketones 12 and 13 may be prepared by acidic cleavage of those spiro<4.4>acetals lacking 2,7-substituents.

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

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Monomeric metal aqua complexes in the interlayer space of montmorillonites as strong Lewis acid catalysts for heterogeneous carbon-carbon bond-forming reactions

Montmorillonite-enwrapped copper and scandium catalysts (Cu2– and Sc3+-monts) were easily prepared by treating Na–mont with the aqueous solution of the copper nitrate and scandium triflate, respectively. The resulting Cu2+- and Sc3+-monts showed outstanding catalytic activities for a variety of carbon-carbon bond-forming reactions, such as the Michael reaction, the Sakurai-Hosomi allylation, and the Diels-Alder reaction, under solvent-free or aqueous conditions. The remarkable activity of the mont catalysts is attributable to the negatively charged silicate layers that are capable of stabilizing metal cations. Furthermore, these catalysts were reusable without any appreciable loss in activity and selectivity. The Cu2+-mont-catalyzed Michael reaction proceeds via a ternary complex in which both the 1,3-dicarbonyl compound and the enone are coordinated to a Lewis acid Cu2+ center.

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

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Design and Synthesis of 2,3- trans-Proline Analogues as Ligands for Ionotropic Glutamate Receptors and Excitatory Amino Acid Transporters

Development of pharmacological tools for the ionotropic glutamate receptors (iGluRs) is imperative for the study and understanding of the role and function of these receptors in the central nervous system. We report the synthesis of 18 analogues of (2S,3R)-2-carboxy-3-pyrrolidine acetic acid (3a), which explores the effect of introducing a substituent on the ?-carbon (3c-q). A new synthetic method was developed for the efficient synthesis of racemic 3a and applied to give expedited access to 13 racemic analogues of 3a. Pharmacological characterization was carried out at native iGluRs, cloned homomeric kainate receptors (GluK1-3), NMDA receptors (GluN1/GluN2A-D), and excitatory amino acid transporters (EAAT1-3). From the structure-activity relationship studies, several new ligands emerged, exemplified by triazole 3p-d1, GluK3-preferring (GluK1/GluK3 Ki ratio of 15), and the structurally closely related tetrazole 3q-s3-4 that displayed 4.4-100-fold preference as an antagonist for the GluN1/GluN2A receptor (Ki = 0.61 muM) over GluN1/GluN2B-D (Ki = 2.7-62 muM).

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

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Ytterbium(III) trifluoromethanesulfonate-catalyzed homoconjugate addition reactions of beta-ketoesters with activated cyclopropane derivatives at high pressure

Ytterbium(III) triflate was found to be an effective catalyst for the homo-conjugate addition reaction of beta-ketoesters with diethyl cyclopropanedicarboxylate at high pressure.

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

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Highly Enantioselective Intermolecular Cu(I)-Catalyzed Cyclopropanation of Cyclic Enol Ethers. Asymmetric Total Synthesis of (+)-Quebrachamine

A set of cyclic enol ethers derived from 2,3-dihydrofuran 35 and 3,4-dihydropyran 8 with a varying substitution pattern at the olefinic system were synthesized. Evans’s ligand 5 with Cu(I)OTf was found to be an effective catalyst in the cyclopropanation reaction between cyclic enol ethers 14, 19, 28-31, and 33 and ethyl diazoacetate 6 to give diastereoselectivities up to exo/endo = 95:5 and enantioselectivities higher than 95% in nearly all cases. Because of the selective building of a quarternary carbon center and good yields in the formation of bicyclic structures 34c-h, the reaction was used as a key step in the asymmetric synthesis of (+)-quebrachamine 7, an indole alkaloid of the Aspidosperma family. After acid-induced ring opening of bicyclic compound 34f to lactone 40 followed by LiAlH4 reduction to the masked aldehyde 41, a reaction with tryptamine gave intermediate 42. This alcohol was efficiently converted into the indole alkaloid (+)-quebrachamine 7 in an overall yield of 37% starting from the chiral synthon 34f. Moreover it revealed the absolute configuration of the quarternary center of the cyclopropanation product 34f to be S.

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

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COMPOUNDS, COMPOSITIONS, AND METHODS

The present disclosure relates generally to LRRK2 inhibitors, or a pharmaceutically acceptable salt, deuterated analog, prodrug, tautomer, stereoisomer, or mixture of stereoisomers thereof, and methods of making and using thereof.

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

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Bis(trimethylsilyl) Sulfate Catalysis in gamma-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on alpha-Carbon

The title reaction of 1-carbonyl substituted cyclopropanecarboxylates proceeds under C(1)-C(2) bond cleavage to produce gamma-lactones.Stereochemically, the reaction takes two pathways: (1) substrates with a cationstabilizing group like vinyl on C(2) give thermodynamically favored gamma-lactones having the thermodynamically more stable arrangement of substituents irrespective of the configuration of the cyclopropane substrates, (2) substrates without such a cation-stabilizing group afford gamma-lactones under ca. 70percent inversion at C(2) reaction center.

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

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Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts

Figure presented Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.

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

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New Methods for Stereoselective Synthesis of alpha-Alkylidene-gamma-butyrolactones Using Monoanion of O-Ethyl S-(Tetrahydro-2-oxo-3-furanyl) Thiocarbonate and Dianion of alpha-Mercapto-gamma-butyrolactone

The lithium enolates of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate and thiocarbonate were found to be efficient reagents for the stereoselective synthesis of alpha-alkylidene-gamma-butyrolactones from carbonyl compounds.The dianion of alpha-mercapto-gamma-butyrolactone was successfully generated by treatment of alpha-mercapto-gamma-butyrolactone with 2.2 equivalents of lithium diisopropylamide in the presence of N,N,N’,N’-tetramethylethylenediamine at -78 deg C in THF.The dianion thus formed has been utilized for the efficient and stereoselective synthesis of alpha-alkylidene-gamma-butyrolactones from carbonyl compounds.

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

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Azidation of beta-carbonyl lactones and lactams

The direct azidation of various heterocyclic beta-ketoesters, lactones, and lactams is reported. By using tosylazide and an organic base such as l-proline or TBD, the direct alpha-insertion of azide into these substrates was achieved in moderate to good yields, without competitive deacylating diazo transfer. This procedure represents an interesting alternative to the usual two-step approach of alpha-halogenation and subsequent displacement with azide ion.

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