Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition DOI

Yabo Deng,

Yongzhen Li,

Yalan Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(1), P. 210 - 215

Published: Nov. 24, 2021

A novel kind of CF 2 H-containing dispiro[benzo[ b ]thiophene-oxindole-pyrrolidine] has been achieved via an organocatalyzed 1,3-dipole reaction.

Language: Английский

Stereoselective synthesis and applications of spirocyclic oxindoles DOI Creative Commons
Alexander J. Boddy, James A. Bull

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(5), P. 1026 - 1084

Published: Jan. 1, 2021

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

Language: Английский

Citations

260
Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles DOI
Yongchao Wang, Angel A. Cobo, Annaliese K. Franz

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(15), P. 4315 - 4348

Published: Jan. 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.

Language: Английский

Citations

170
Enantioselective Synthesis of Spirosilabicyclohexenes by Asymmetric Dual Ring Expansion of Spirosilabicyclobutane with Alkynes DOI
Hua Chen,

Ju Peng,

Qinjiao Pang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(48)

Published: Oct. 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.

Language: Английский

Citations

50
An update on the progress of cycloaddition reactions of 3-methyleneindolinones in the past decade: versatile approaches to spirooxindoles DOI
Ruqaiya Saeed, Akash P. Sakla, Nagula Shankaraiah

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(36), P. 7768 - 7791

Published: Jan. 1, 2021

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

Language: Английский

Citations

43
Stereoselective Domino Reactions in the Synthesis of Spiro Compounds DOI
Maurizio Benaglia, Sandro J. Greco,

Regina Westphal

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(13), P. 2927 - 2975

Published: Feb. 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

Language: Английский

Citations

29
Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles DOI
Qing‐Feng Li, Jing Ma,

Junjia Meng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4412 - 4439

Published: Nov. 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.

Language: Английский

Citations

14
Strategies and methodologies for the construction of spiro-γ-lactams: an update DOI
Américo J. S. Alves, Nuno G. Alves, Maria I. L. Soares

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(13), P. 3543 - 3593

Published: Jan. 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.

Language: Английский

Citations

31
Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles DOI
Biplob Borah, Samrita Sharma, L. Raju Chowhan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(3)

Published: Feb. 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.

Language: Английский

Citations

12
Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles DOI
Wang Bi,

Jing-Kun Gao,

Shuo Sun

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3739 - 3743

Published: April 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.

Language: Английский

Citations

4
Base-Promoted [3+2]-Cycloaddition of N-Alkoxy-4-Oxo-Acrylamides with Isatins for Stereoselective Synthesis of Spirooxindole-2-Oxazolidinones DOI
Sung‐Gon Kim,

Yeongju Kim

Published: Jan. 1, 2025

Language: Английский

Citations

0