Advances in heterocycle synthesis through photochemical carbene transfer reactions

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2125 - 2136

Published: Jan. 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.

Language: Английский

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Lewis-Base-Catalyzed Enantioselective Formal [4 + 2] Annulations of Morita–Baylis–Hillman Carbonates: Access to Tetrahydroquinolines Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3347 - 3351

Published: May 10, 2023

The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of o-acylamino-aryl MBH carbonates and electron-deficient olefins was developed. Tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter were obtained in high yields good enantioselectivity.

Language: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

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Dearomative [4 + 2] cycloaddition of 3‐nitroindoles with ortho‐amino Morita−Baylis−Hillman carbonates to forge indole‐fused quinolines

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(3), P. 528 - 537

Published: Jan. 16, 2024

Abstract A dearomative [4 + 2] cycloaddition of 3‐nitroindoles ortho ‐amino Morita−Baylis−Hillman carbonates was established under mild conditions. This method provides an efficient and practical approach for delivering tetrahydro‐5 H ‐indolo[2,3‐ b ]quinolines containing three contiguous stereocenters, two tertiary one quaternary, in high yield (up to 95%) with excellent diastereoselectivity (all cases >25:1 dr ). The potential synthetic applications this strategy were also highlighted by the scale‐up experiment further transformation. Moreover, structure relative configuration cycloadduct unequivocally confirmed single‐crystal X‐ray diffraction.

Language: Английский

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Recent Advances in the Reaction of MBH Carbonates: Scope and Mechanism

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: June 27, 2024

Abstract In recent years, Morita‐Baylis‐Hillman (MBH) carbonates have been extensively used in domino reactions for the synthesis of novel cyclic and acyclic compounds. This review highlights progress made last decade a series compounds from an uncyclized reaction or annulation MBH carbonates, which demonstrates that excellent reactivity high research value as representative substrates organic synthesis. We hope summary understanding can inspire chemists to apply these design more efficient reactions, will be beneficial drug chemistry.

Language: Английский

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Divergent Synthesis of Highly Substituted Tetrahydroquinolines and Cyclopentenes via Lewis Base Catalyzed Switchable [4 + 2] and [3 + 2] Annulations of MBH-Carbonates with Activated Olefins

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5982 - 5996

Published: April 20, 2023

A highly selective and divergent synthesis which enabled access to various complex compounds is attractive in organic medicinal chemistry. Herein, we developed an effective method for of substituted tetrahydroquinolines via Lewis base catalyzed switchable annulations Morita-Baylis-Hillman carbonates with activated olefins. The reaction displayed [4 + 2] or [3 catalyst substrate control, providing a diverse range architectures contained cyclopentenes three contiguous stereocenters bearing quaternary carbon center high yields excellent diastereoselectivities regioselectivities. Furthermore, synthetic utility this strategy was further highlighted by gram-scale experiments simple transformations the products.

Language: Английский

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Visible-light-mediated substituent-controlled regiodivergent (2 + 2)/(3 + 2) cycloadditions for the synthesis of aza-analogs of β-lactam and γ-fused lactam derivatives

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3576 - 3582

Published: Jan. 1, 2024

Substituent-controlled regiodivergent synthesis of aza-analogs β-lactam and γ-fused lactam derivatives via the visible-light-induced Wolff rearrangement α-diazoketones azo esters.

Language: Английский

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Lewis Base Controlled (4 + 3) and (4 + 2) Annulations of MBH Carbonates with Benzofuran‐derived Azadienes: Access to Highly Substituted Benzofuro[3,2‐b]azepines and Spirotetrahydroquinolines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4521 - 4527

Published: Aug. 7, 2024

Abstract Catalyst‐controlled switchable (4+3) and (4+2) annulation reactions of Morita–Baylis–Hillman carbonates with benzofuran‐derived azadienes have been established. Employing PCy 3 as the catalyst, reaction could provide a variety synthetically useful benzofuro[3,2‐ b ]azepines in good yields (80–92%) excellent chemo‐ regioselectivities via cycloaddition reactions. Whereas changing catalyst from to DMAP, were switched construct highly substituted spirotetrahydroquinoline scaffolds three sequential stereocenters containing all‐carbon spiro‐quaternary efficiency diastereoselectivities (92–96% all cases>25:1 dr ) annulations. In addition, synthetic utility this method was further showcased by gram‐scale transformations product.

Language: Английский

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

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4474 - 4487

Published: Jan. 1, 2023

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

Language: Английский

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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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