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Copper catalyzed asymmetric propargylation of aldehydes

The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H812O – PubChem

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A brief synthesis of 2,2?-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) catalyzed by TEAOH in various solvents

Aims and Objectives: 2,2?-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) having four carbonyl functionalities along with their tautomeric keto-enol forms, is an important biologically active compound and important synthetic intermediate in the synthesis of xanthenes. This study was conducted in order to develop a new and concise method of synthesis of 2,2?-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives. Materials and Methods: TEAOH (20 mol %) was fond to be as a simple and efficient catalyst for the preparation of 2,2?-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives by the Knoevenagel condensation/Michael addition tandem reactions. Results: A concise and practical method was developed for one-pot synthesis of 2,2?-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives catalyzed by TEAOH at room temperature in various solvents. Conclusion: This strategy provides several advantages over the traditional synthetic method, and is applicable to a wide variety of aromatic and heteroaromatic aldehydes at room temperature in various solvents.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H825O – PubChem

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Sequential enzymatic procedure for the preparation of enantiomerically pure 2-heteroaryl-2-hydroxyacetic acids

Starting from the racemic 2-benzofuranyl- and 2-benzo[b]thiophenyl-2- hydroxyacetic acid ethyl esters as substrates, a general method was developed for the efficient synthesis of the corresponding highly enantiomerically enriched (ee up to 99%) (R)- and (S)-2-heteroaryl-2-hydroxyacetic acids.

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Benzofuran – Wikipedia,
Benzofuran | C8H968O – PubChem

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Asymmetric synthesis and bioselective activities of alpha-amino-phosphonates based on the dufulin motif

The asymmetric synthesis of enantiomerically pure alpha-aminophosphonates with high and bioselective activities is a challenge. Here, we report that both enantiomers of alpha-aminophosphonates bearing the N-benzothiazole moiety can be prepared in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) by using chiral thiourea organocatalysts. Evaluation of the antiviral activities of our reaction products against cucumber mosaic virus (CMV) led to promising hits with high and selective biological activities, wherein (R)-enantiomers exhibit higher biological activities than the corresponding (S)-enantiomers. Especially, compound (R)-3b with excellent anti-CMV activity (curative activity, 72.3%; protection activity, 56.9%; and inactivation activity, 96.9%) at 500 mug/mL emerged as a potential inhibitor of the plant virus. The difference in the selective bioactivity could be affected by the combination mode of the three-dimensional space between the enantiomers of alpha-aminophosphonate and cucumber mosaic virus coat protein (CMV-CP) via florescence spectroscopy and molecular docking.

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Benzofuran – Wikipedia,
Benzofuran | C8H1130O – PubChem

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Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes

We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-alpha-alkyl intermediates to various aldehydes including alpha,beta-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, alpha,beta-unsaturated aldehydes were successfully used as electrophiles in Cu?H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H864O – PubChem

Awesome Chemistry Experiments For 4265-16-1

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Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles

A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4?C7 positions of indoles and related heterocycles.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H926O – PubChem

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Design, synthesis and biological evaluation of new embelin derivatives as CK2 inhibitors

A new series of furan embelin derivatives was synthesized and characterized as ATP-competitive CK2 inhibitors. The new compounds were efficiently synthesized using a multicomponent approach from embelin (1), aldehydes and isonitriles through a Knoevenagel condensation/Michael addition/heterocyclization. Several compounds with inhibitory activities in the low micromolar or even submicromolar were identified. The most active derivative was compound 4l (2-(tert-butylamino)-3-(furan-3-yl)-5-hydroxy-6-undecylbenzofuran-4,7-dione) with an IC50 value of 0.63 muM. It turned out to be an ATP competitive CK2 inhibitor with a Ki value determined to be 0.48 muM. Docking studies allowed the identification of key ligand-CK2 interactions, which could help to further optimize this family of compounds as CK2 inhibitors.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H723O – PubChem

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Sc(OTf)3-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products

The addition of bromomagnesium 2-vinyloxy ethoxide to various aldehydes in the presence of 10 mol% Sc(OTf)3 provides a broad range of functionalized protected aldol compounds. The enantioselective preparation of these aldols can be achieved via a Swern oxidation-CBS reduction sequence. Use of the dioxolane derived from 2-bromocyclohexanone provides the expected aldol product as the anti diastereoisomer (dr >99:1).

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1009O – PubChem

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Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis

The chromium photocatalyzed cyclopropanation of diazo reagents with electron-rich alkenes is described. The transformation occurs under mild conditions and features specific distinctions from traditional diazo-based cyclopropanations (e.g., avoiding beta-hydride elimination, chemoselectivity considerations, etc.). The reaction appears to work most effectively using chromium catalysis, and a number of decorated cyclopropanes can be accessed in generally good yields.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1029O – PubChem

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Iridium-catalyzed Synthesis of Saturated N-Heterocycles from Aldehydes and SnAP Reagents with Continuous Flow Photochemistry

Commercially available tin amine protocol (SnAP) reagents provide a simple approach to the synthesis of a wide variety of saturated N-heterocycles from aldehydes. In this report, we disclose that the copper(II) promoter and hexafluoroisopropanol can be replaced by photocatalytic conditions using Ir[dF(CF3)ppy]2(dtbbpy)PF6 in CH3CN. Continuous flow photochemical conditions provide a clean, scalable approach to valuable products including morpholines, piperazines, thiomorpholines, diazepanes, and oxazepanes from aldehyde starting materials.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H871O – PubChem