Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4412 - 4439

Опубликована: Ноя. 16, 2023

Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.

Язык: Английский

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Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides

Advanced Science, Год журнала: 2023, Номер 10(35)

Опубликована: Окт. 23, 2023

Abstract Herein, the first diversity‐oriented catalytic asymmetric dearomatization of indoles with o ‐quinone diimides ( ‐QDIs) is reported. The (CADA) one research focuses in terms structural and biological importance dearomatized indole derivatives. Although great achievements have been made target‐oriented CADA reactions, reactions are regarded as more challenging remain elusive due to lack synthons featuring multiple reaction sites difficulty precise control chemo‐, regio‐, enantio‐selectivity. In this work, ‐QDIs employed a versatile building block, enabling chemo‐divergent dearomative arylation [4 + 2] cycloaddition indoles. Under catalysis chiral phosphoric acid mild conditions, various indolenines, furoindolines/pyrroloindolines, six‐membered‐ring fused indolines collectively prepared good yields excellent enantioselectivities. This synthesis protocol enriches chemistry offers new opportunities for reactions.

Язык: Английский

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Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles

Chinese Chemical Letters, Год журнала: 2023, Номер 35(4), С. 108830 - 108830

Опубликована: Июль 27, 2023

Язык: Английский

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Catalytic asymmetric de novo construction of 4-pyrrolin-2-ones via intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones

Chemical Communications, Год журнала: 2023, Номер 59(39), С. 5902 - 5905

Опубликована: Янв. 1, 2023

The chiral phosphoric acid-catalyzed asymmetric intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones has been established. This convergent protocol leads to a facile and enantioselective de novo construction wide range fully substituted 4-pyrrolin-2-ones bearing carbon atom in good yields excellent enantioselectivities (26 examples, 72-95% 87-99% ee).

Язык: Английский

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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(18), С. 2223 - 2227

Опубликована: Май 14, 2024

Comprehensive Summary Allenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties organic compounds make allenes a desirable choice various applications. Here, we report facile method for atom‐economical synthesis propargyl allenylamines via underdeveloped [2,3]‐sigmatropic rearrangement. Our strategy employs easily accessible propargylamines starting materials, which first converted into ammonium salts, followed by base‐promoted This one‐pot, two‐step reaction proceeds absence transition metals, displays very broad scope, does not require introduction electron‐withdrawing group materials.

Язык: Английский

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Catalytic Asymmetric Rearrangement of Azoalkene-Derived Sulfonium Ylides via Remote Chirality Control

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 26, 2025

The [2,3]-sigmatropic rearrangement has been widely utilized to construct C-S bonds. Herein, we report an enantioselective, intermolecular, and noncarbenoid of sulfonium ylides using azoalkenes. This process features a broad substrate scope, high efficiency, excellent enantioselectivity, achieving yields up 99% enantiomeric excess (ee) 96%. Furthermore, the protocol demonstrated good scalability.

Язык: Английский

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Catalytic asymmetric interrupted Attanasi reaction: access to fused 2,3-dihydropyrroles with vicinal quaternary carbons

Chemical Communications, Год журнала: 2023, Номер 59(52), С. 8103 - 8106

Опубликована: Янв. 1, 2023

The first catalytic asymmetric interrupted Attanasi reaction has been established. Under the catalysis of a bifunctional organocatalyst, condensation cyclic β-keto esters with azoalkenes readily occurred, delivering variety bicyclic fused 2,3-dihydropyrroles vicinal quaternary stereogenic centers in good yields and to excellent enantioselectivities (27 examples, up 96% yield 95% ee).

Язык: Английский

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Catalyst-free racemic and H₂O/CPA-catalyzed asymmetric regio-reversed domino processes of triketone enones with azlactones

Green Chemistry, Год журнала: 2023, Номер 25(14), С. 5692 - 5697

Опубликована: Янв. 1, 2023

The first regio-reversed domino processes of triketone enones with azlactones are established leading to the formation a variety bicyclic furofurans bearing vicinal quaternary carbons in good excellent yields.

Язык: Английский

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Visible light-induced organo-photocatalyzed route to synthesize substituted pyrazoles

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2384 - 2388

Опубликована: Янв. 1, 2024

Herein we developed an efficient organo-photocatalytic method to synthesize tetra-substituted pyrazole derivatives using azoalkenes via [4 + 1] annulation strategy with in situ generated acyl radical visible-light under milder reaction conditions.

Язык: Английский

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