Stereoselective synthesis and applications of spirocyclic oxindoles

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(5), С. 1026 - 1084

Опубликована: Янв. 1, 2021

This review summaries recent synthetic developments towards spirocyclic oxindoles and applications as valuable medicinal targets.

Язык: Английский

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Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(15), С. 4315 - 4348

Опубликована: Янв. 1, 2021

Catalytic asymmetric MCCRs for enantioselective synthesis of spirooxindoles by using chiral phosphoric acids, amines, bifunctional thiourea/squaramides and metal-based reagents as catalysts.

Язык: Английский

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Enantioselective Synthesis of Spirosilabicyclohexenes by Asymmetric Dual Ring Expansion of Spirosilabicyclobutane with Alkynes

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(48)

Опубликована: Окт. 7, 2022

Silaspiranes have attracted particular attention due to their chiral spiro-silicon center, which serves as an ideal carbon isostere and can endow spiro-analogs with distinct properties. Distinct from previously reported cyclization or cycloaddition strategies form 5/5-silaspiranes, we report herein the asymmetric dual ring expansion of spirosilabicyclobutanes alkynes synthesize axially spirosilabicyclohexenes bearing a novel 6/6-silaspirane framework. DFT (density functional theory) calculations provide deep insight into origin high enantioselectivity controlled by sterically demanding binaphthyl phosphoramidite ligand. Preliminary studies chiroptical properties indicate that one spirosilabicyclohexene analogs exhibit fluorescence emission, Cotton effects CPL (circularly polarized luminescence) activity.

Язык: Английский

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An update on the progress of cycloaddition reactions of 3-methyleneindolinones in the past decade: versatile approaches to spirooxindoles

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(36), С. 7768 - 7791

Опубликована: Янв. 1, 2021

This review focuses on important cycloaddition reactions of 3-methyleneindolinones to afford 3,3′-spirocyclic oxindoles.

Язык: Английский

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Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Synthesis, Год журнала: 2022, Номер 54(13), С. 2927 - 2975

Опубликована: Фев. 14, 2022

Abstract This review summarizes the latest developments in asymmetric domino reactions, with emphasis on preparation of spiro compounds. Discussions stereoselectivity transformations, reaction mechanisms, rationalization stereochemical outcome, and applications reactions to synthesis biologically active molecules natural products are included when appropriate. 1 Introduction 2 Asymmetric Domino Reactions 2.1 Initiated by Michael 2.2 Mannich 2.3 Knoevenagel 2.4 Cycloaddition 2.5 Metal Insertion 2.6 Other Mechanisms 3 Conclusion

Язык: Английский

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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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Strategies and methodologies for the construction of spiro-γ-lactams: an update

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(13), С. 3543 - 3593

Опубликована: Янв. 1, 2021

This review gives an insight into the most recent synthetic methodologies towards spiro-γ-lactams, a class of compounds that are present in wide range bioactive and naturally occurring molecules.

Язык: Английский

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Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(3)

Опубликована: Фев. 3, 2023

Abstract Spirocyclic compounds, particularly spirooxindoles that comprise a tetrahedral sp 3 ‐hybridized carbon atom at the C‐3 position of an orthogonally shaped bicyclic structure have recently received increasing attention in drug discovery and development, besides their major potential natural products synthetic organic chemistry. They are found to be structural constituents many alkaloids, key active building blocks for construction various pharmaceutically significant molecules. On other hand, with awareness people about protecting health living environment from pollution caused by chemical laboratories industry, development method provides alternatives traditional one introducing economical sustainable processes is scientifically technically demanding but challenging. To address these concerns inspired photosynthesis process, visible light‐induced chemistry appears highly economic, sustainable, alternative approach synthesis. The present mini‐review aims highlight recent progress accomplished straightforward accelerated light irradiation period 2015 date. Besides reviewing advantages achieved this field, we also attempt find out drawback, mechanistic rationalization, scopes future applications.

Язык: Английский

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Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3739 - 3743

Опубликована: Апрель 29, 2024

An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N-(o-bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba)2/SPINOL-based phosphoramidite as the chiral catalyst and HCO2Na hydride source, a series enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The formal tetrasubstituted alkene β-hydrogens therefore realized by inhibiting β-H elimination.

Язык: Английский

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Base-Promoted [3+2]-Cycloaddition of N-Alkoxy-4-Oxo-Acrylamides with Isatins for Stereoselective Synthesis of Spirooxindole-2-Oxazolidinones

Опубликована: Янв. 1, 2025

Язык: Английский

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