Advances in heterocycle synthesis through photochemical carbene transfer reactions

Chemical Communications, Год журнала: 2024, Номер 60(16), С. 2125 - 2136

Опубликована: Янв. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Язык: Английский

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Catalytic asymmetric photocycloaddition reactions mediated by enantioselective radical approaches

Chemical Society Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

The use of olefins in the construction cyclic compounds represents a powerful strategy for advancing pharmaceutical industry.

Язык: Английский

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Asymmetric Trapping of Siloxyketenes In Situ Generated from [1,3]-Silyl Migration of α-Ketoacylsilanes: A Visible-Light-Driven Palladium-Catalyzed [4 + 2] Cycloaddition

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 5796 - 5805

Опубликована: Март 25, 2025

The transition metal-catalyzed asymmetric [n + 2] cycloaddition reaction with oxy-substituted ketene intermediates remains a synthetic challenge due to the limited availability of suitable precursors. Herein, we report visible-light-driven, palladium-catalyzed [4 vinyl benzoxazinanones siloxyketene intermediates, generating structurally diverse chiral quinolinone derivatives satisfactory diastereo- and enantioselectivities. transient generation siloxyketenes from α-ketoacylsilylanes through visible-light-induced Brook rearrangement is important for success present cycloaddition. 13C-labeling experiments reveal pathway involving [1,3]-silyl migration process. side arm effects BOX ligand silyl steric hindrance α-ketoacylsilanes play crucial roles in stereoselectivity control, theoretical calculations provide insights into stereochemical outcome reaction.

Язык: Английский

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Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 1034 - 1041

Опубликована: Янв. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Язык: Английский

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Visible-light-induced [1,3]-brook rearrangements of α-ketoacylsilanes and their subsequent trapping in a tandem annulation with 1,3,5-triazinanes and azomethine imines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3250 - 3256

Опубликована: Янв. 1, 2024

An unusual visible-light-induced [1,3]-brook rearrangement of α-ketoacylsilanes for cascade cyclization with 1,3,5-triazinanes and C , N -cyclic azomethine imines has been realized to assemble various β-lactams pyrazolidinone scaffolds.

Язык: Английский

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Lighting the way to diverse cyclic architectures: expanding the horizons with photogenerated ketenes in sustainable chemistry

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4474 - 4487

Опубликована: Янв. 1, 2023

Photogenerated ketenes simplify and accelerate the synthesis of diverse cyclic architectures demonstrate their promising applications in flow chemistry.

Язык: Английский

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Pd-catalyzed enantioselective [4 + 4] dipolar cycloaddition of aliphatic 1,4-dipoles with azadienes to access eight-membered N-heterocycles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4698 - 4702

Опубликована: Янв. 1, 2023

A novel asymmetric [4 + 4] dipolar cycloaddition of aliphatic 1,4-dipoles with azadienes was developed to construct chiral benzofuran- and indene-fused eight-membered N-heterocycles in good yields excellent stereoselectivities.

Язык: Английский

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Inherently Chiral Seven- and Eight-Membered Rings: Enantioselective Synthesis and Applications

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

Compared to smaller or larger rings, seven- and eight-membered carbo- heterocycles are typically nonplanar exhibit greater conformational rigidity. This property alone can impart chirality certain 7- 8-membered ring systems. Herein, we summarize recent achievements in the enantioselective synthesis of this class inherently chiral medium including both construction modification, as well applications ligands catalysts derived from these rigid cyclic scaffolds asymmetric catalysis.

Язык: Английский

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Photoinduced Wolff Rearrangement for Synthesizing Chiral Heterocycles

Topics in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1780 - 1787

Опубликована: Янв. 1, 2023

Biologically active [1,5]diazocino[2,1- b ]quinazolinones were synthesized via base-promoted [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza- ortho -quinone methides.

Язык: Английский

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