Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3810 - 3815

Опубликована: Апрель 28, 2024

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.

Язык: Английский

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Recent Advances in Palladium-Catalyzed [4 + n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes

Topics in Current Chemistry, Год журнала: 2023, Номер 381(6)

Опубликована: Ноя. 3, 2023

Язык: Английский

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Modular Synthesis of Planar-Chiral Cyclononenes via trans-Retentive Trapping of π-Allyl-Pd Dipoles

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Янв. 17, 2025

Trans-cycloalkenes are abundant in bioactive natural products and have been used as powerful tools chemical biology drug discovery. However, strategies for the modular synthesis of trans-cycloalkenes, especially planar-chiral medium-sized ones, with high efficiency selectivity, still remain elusive. Herein, we report a Pd-catalyzed asymmetric [7 + 2] cyclization strategy to address this challenge. As result, two types trans-cyclononenes bearing all-carbon chiral quaternary stereocenters produced up 85% yield, >99% ee, >19:1 dr (42 examples). The key success is maintenance trans-2H configuration π-allyl-Pd species along unusual linear selectivity during H-bond-assisted process. In addition, conversion planar chirality central its application selective bioimaging cancer cells via bioorthogonal reaction were performed demonstrate synthetic value methodology.

Язык: Английский

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Synthesis of 8-membered trifluoromethyl benzoxazocines via a Pd-catalyzed ring-expansion reaction of trifluoromethyl benzoxazinones with 2-methylidenetrimethylene carbonate and mechanistic investigations

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A Pd-catalyzed ring-expansion reaction of trifluoromethyl benzoxazinones with 2-methylidenetrimethylene carbonate to access 8-membered benzoxazocines is reported.

Язык: Английский

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Pd-Catalyzed [4 + 1] Annulation Strategy to Functionalized 4-Methyleneproline Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1552 - 1555

Опубликована: Янв. 23, 2024

A Pd-catalyzed formal [4 + 1] cycloaddition reaction of sulfur ylides and in situ-generated Pd-stabilized zwitterions offers a convenient route to series functionalized proline derivatives. The utility this method is demonstrated by gram-scale synthesis chemoselective functionalization proline-based derivative.

Язык: Английский

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Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(17), С. 2767 - 2788

Опубликована: Июль 10, 2023

Abstract Chiral aza ‐heterocycles, as a sort of key frameworks natural products et al , are deeply concerned by synthetic chemists. In recent years, catalytic asymmetric reactions several types zwitterionic intermediates, originating form benzoxazinone derivatives, have become popular and efficient approach to obtain chiral ‐heterocycles. Given that, this review attempts summarize development in the field derivatives powerful dipole precursors for construction past various their been developed. Herein, is organized display important potentials values.

Язык: Английский

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Ligand-Controlled Diastereodivergency in Propargylic Alkylation of Vinylogous Aza-Enamines: Construction of 1,3-Stereocenters

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7304 - 7309

Опубликована: Окт. 2, 2023

The first diastereodivergent propargylic alkylation reaction is developed. This Cu(I)-catalyzed formal decarboxylative [4+2] cycloaddition between ethynyl benzoxazinanone and vinylogous aza-enamine delivers each diastereomer of tetrahydroquinoline derivatives, bearing 1,3-stereocenters, using either i-Pr-Pybox or BINAP as the ligand under otherwise identical conditions. application aza-enamines in a transition metal-catalyzed transformation example creation 1,3-stereocenters substitution reaction.

Язык: Английский

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Synthetic strategies for the construction of C3–N1′ bisindoles

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(9), С. 1756 - 1764

Опубликована: Янв. 1, 2024

C3-N1' bisindoles are unique structures, and the construction of these structures has drawn much attention. However, their synthesis still presents significant challenges that limit functional group compatibility. This minireview summarizes recent progress in methodology for constructing bisindoles. There two approaches access to bisindoles: (1) direct including reverse polarity techniques. (2) Stepwise using designed prefunctionalized substrates enable further functionalization by additional reactions facilitate target products. I believe this review will allow its readers develop novel

Язык: Английский

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Copper-catalyzed reaction of benzoxazinanones with sulfilimines: access to 2-ethynyl-benzoimidazoles via an abnormal skeletal rearrangement

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(22), С. 4583 - 4586

Опубликована: Янв. 1, 2023

A copper-catalyzed reaction of benzoxazinanones with sulfilimines has been described, and 2-ethynyl-benzoimidazoles were obtained in good yields via an abnormal skeletal rearrangement.

Язык: Английский

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Rh(III)-Catalyzed C–H Activation of Benzamides and Chemodivergent Annulation with Benzoxazinanones: Substrate Controlled Selectivity

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7083 - 7088

Опубликована: Сен. 25, 2023

Decarboxylative annulation of propargyl carbamates with benzamides has been realized via rhodium-catalyzed C-H bond activation under mild conditions, delivering two distinct classes heterocycles in high efficiency and selectivity substrate control. This protocol provides a direct synthetic method for the preparation functionalized 1,8-naphthyridines isoindolinones.

Язык: Английский

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