DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9322 - 9327

Published: Oct. 24, 2024

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.

Language: Английский

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Asymmetric 2,4-Dienylation/[4 + 2] Annulation Cascade to Construct Fused Frameworks via Auto-Tandem Palladium Catalysis

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3682 - 3686

Published: May 16, 2023

A palladium catalyzed tandem reaction between ortho-functionalized aryl enones and 2,4-dienyl carbonates has been presented, proceeding through sequential 2,4-dienylation/Michael addition/π-σ-π isomerization/allylic alkylation. broad array of enantioenriched architectures having fused spirocyclic frameworks are constructed in moderate to excellent yields stereoselectivity. Notably, the intrinsic intramolecular Diels-Alder pattern dienylated intermediates is well reversed via Pd(0)-π-Lewis base catalysis.

Language: Английский

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Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959

Published: May 30, 2024

Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.

Language: Английский

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Regioselective construction of 2-substituted indolines enabled by a rhodium-catalyzed decarboxylation–hydroacylation sequence

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5495 - 5501

Published: Jan. 1, 2024

Rhodium( i )-catalyzed sequential decarboxylation and hydroacylation of vinyl benzoxazinanones with chelating aldehydes for the highly regioselective synthesis 2-substituted indolines via a new η 2 -Rh complex has been developed.

Language: Английский

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Asymmetric Friedel−Crafts reaction of unsaturated carbonyl-tethered heteroarenes via vinylogous activation of Pd⁰-π-Lewis base catalysis

Chemical Science, Journal Year: 2023, Volume and Issue: 14(39), P. 10867 - 10874

Published: Jan. 1, 2023

A variety of deactivated heteroarenes tethered to an unsaturated carbonyl motif can participate in asymmetric Friedel–Crafts reactions with diverse electrophilic reagents catalysed by a chiral Pd 0 -complex.

Language: Английский

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Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519

Published: Jan. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Language: Английский

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