N-Heterocyclic Carbene-Catalyzed Regio- and Enantioselective C7-Alkylation of 4-Aminoindoles with α-Bromoenals

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1787 - 1791

Published: Feb. 23, 2024

The first carbene-catalyzed regio- and enantioselective indole C7-alkylation reaction between 4-aminoindoles α-bromoenals is disclosed. corresponding products could be obtained in moderate to good yields with excellent enantioselectivities. evaluation of antibacterial activity against Psa revealed that nine the C7-functionalized indoles exhibited superior inhibitory activities compared positive controls TC BT. Our approach provides an efficient strategy introduce a chiral chain into C7 position compounds, potential applications evaluated pesticide development.

Language: Английский

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Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(13), P. 6979 - 6987

Published: March 23, 2024

Potato virus Y (PVY) is an important plant that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized their anti-PVY activities evaluated. Biological activity tests demonstrated many compounds exhibited promising absolute configurations obvious distinctions in bioactivities. Notably, compound (S)-4v displayed excellent curative protective efficacy against PVY, with EC50 values 328.6 256.1 μg/mL, respectively, which superior to those commercial virucide ningnanmycin (NNM, 437.4 397.4 respectively). The preliminary mechanism was investigated determine the difference between two enantiomers 4v compounds. Molecular docking indicated stronger binding affinity coating proteins PVY (PVY-CP) (−6.5 kcal/mol) compared (R)-4v (−6.2 kcal/mol). Additionally, can increase chlorophyll content defense-related enzyme more effectively than its enantiomer. Therefore, this study provides basis development agricultural chemicals.

Language: Английский

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Copper-catalyzed enantioselective desymmetrizing C(sp2)–H functionalization of azide-ynamides via α-imino copper carbenes

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(9), P. 2982 - 2988

Published: July 3, 2024

Language: Английский

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Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(46)

Published: July 25, 2024

Abstract An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single N‐heterocyclic carbene (NHC) catalyst to react the enantiomers of racemic imine substrate in a fashion. distinct and stereoselectivities respectively from same reaction system good excellent yields, enantio‐ diastereoselectivities. Control experiments studies carried out probe dynamic properties during progress. The pyridine lactam show interesting applications both asymmetric synthesis pesticide development.

Language: Английский

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Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 1, 2024

Language: Английский

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Asymmetric construction of axial and planar chirality with N-heterocyclic carbene (NHC) organocatalysis

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Language: Английский

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NHC-mediated photocatalytic para-selective C–H acylation of aryl alcohols: regioselectivity control via remote radical spiro cyclization

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

Language: Английский

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Recent Progress in Chiral Quaternary Ammonium Salt-Promoted Asymmetric Nucleophilic Additions

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1973 - 2001

Published: Jan. 20, 2025

Chiral quaternary ammonium ion-pair organocatalysis has been widely used in the facile synthesis of chiral molecules with challenging stereocenters. Especially, numerous asymmetric nucleophilic addition reactions have facilitated this strategy. This review systematically summarizes additions promoted by salts past decade. The content is organized according to types electrophiles involved these catalytic transformations. Our own perspectives on future development within highly active research field are also provided.

Language: Английский

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Construction of axial and point chirality through Ni-catalyzed sila-cycloaddition reaction via desymmetrization and (dynamic) kinetic resolution

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

Language: Английский

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Access to Chiral Dihydro-1,4-Benzoxazine-2-Carboxylates through NHC-Catalyzed Dynamic Kinetic Resolution

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

A chiral carbene-catalyzed dynamic kinetic resolution for the facile synthesis of enantioenriched dihydro-1,4-benzoxazine-2-carboxylates is disclosed. The reaction conditions are mild, and a diversity substituents well-tolerated in this transformation. In addition, our methodology also provides an efficient strategy building chromane-2-carboxylate 2,3-dihydro-1,4-benzodioxane-2-carboxylate. optically pure products generated from protocol can be easily derived as key intermediates drugs bioactive molecules.

Language: Английский

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