Iron-Catalyzed 1,3-Dipolar Cycloaddition of Alkynes and Aryl Nitrones for the Synthesis of Chiral ∆4-Isoxazolines

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The synthesis of chiral Δ4-isoxazolines is a crucial area research due to their biological activity and versatility in synthetic chemistry. Driven by the abundant reserves, low cost high biocompatibility iron catalysts, we herein investigated catalytic potential complexes asymmetric 1,3-dipolar cycloaddition reactions between N-Bn,α-aryl nitrones 3-propioloyloxazolidin-2-ones. By utilizing Fe(OTf)2 (S,S)-DBFOX-Ph, series (R)-Δ4-isoxazolines were obtained yields (up 99%) with good excellent enantioselectivities 98 : 2 er). Additionally, using Fe(OTf)3 (±)-BINOL as catalyst, diastereoselectivities >20 1 dr) achieved for (S,S)-Δ4-isoxazoline derivatives from 3-propioloyloxazolidin-2-ones bearing Evans auxiliary. Gram-scale utility also demonstrated.

Language: Английский

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P(═O)R₂-Directed Asymmetric Catalytic C–H Olefination Leading to C–N Axially Chiral Targets

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

Published: March 11, 2025

A novel P(═O)R2-directed asymmetric catalytic olefination has been developed, enabling efficient access to carbon–nitrogen axially chiral products with excellent yields (up 92%) and enantioselectivity 99% enantiomeric excess). The synergistic coordination of phosphine oxide functionality l-pGlu-OH the Pd metal center, serving as an directing group ligand, was key success this C–H functionalization system. reaction demonstrated a broad substrate scope, yielding 33 distinct C–N axial products. absolute configuration unambiguously confirmed via X-ray diffraction analysis. Additionally, three representative applications were showcased, involving reduction oxidation produce phosphines related derivatives. plausible cycle mechanism proposed, supported by detailed experimental studies. Aggregates in system identified aggregation-induced polarization experiments.

Language: Английский

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Chiral phosphoric acid-catalyzed atroposelective oxidative coupling of carbazoles

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

Published: March 14, 2025

Language: Английский

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Chiral Phosphoric Acid‐Catalyzed Enantioselective Synthesis of Axially Chiral Compounds Involving Indole Derivatives

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)

Published: June 26, 2023

Indoles are one of the most ubiquitous subclass N-heterocycles and increasingly incorporated to design new axially chiral scaffolds. The rich profile reactivity N-H functionality allow chemical derivatization for enhanced medicinal, material catalytic properties. Although asymmetric C-C coupling two arenes gives direct access biaryl scaffolds, this chemistry has been remit metal catalysis works efficiently on limited substrates. Our group devoted special interest in devising novel organocatalytic arylation reactions fabricate atropisomers. In realm, indoles derivatives have reliably used as partners combination with azoarenes, nitrosonapthalenes quinone derivatives. Their efficient interaction phosphoric acid catalyst well tunability electronics sterics enabled excellent control stereo-, chemo- regioselectivity furnish diverse addition, could act nucleophiles desymmetrization 1,2,4-triazole-3,5-diones. This account provides a succinct illustration these developments.

Language: Английский

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Machine learning for predicting enantioselectivity in chiral phosphoric acid-catalyzed naphthyl-indole synthesis

Journal of Chemical Sciences, Journal Year: 2025, Volume and Issue: 137(2)

Published: April 7, 2025

Language: Английский

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