New thiourea organocatalysts and their application for the synthesis of 5-(1<i>H</i>-indol-3-yl)methyl-2,2-dimethyl-1,3-dioxane-4,6-diones a source of chiral 3-indoylmethyl ketenes

Najda-Mocarska, Ewelina; Zakaszewska, Anna; Janikowska, Karolina; Makowiec, Sławomir

doi:10.1080/00397911.2017.1383432

Cited by 6 publications

(4 citation statements)

References 16 publications

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Section: Conjugate Addition To Electrophilic C�c Bondsmentioning

confidence: 99%

“…Consequently, formation of chelate complex between the two imide carbonyls with the metal cation facilitated differentiating enantiotopic faces of the reacting double bond, resulting in enhanced enantioselectivity (Scheme a). In another study, Mocarska et al reported a series of thiourea-based organocatalysts for the preparation of chiral 5-((1 H -indol-3-yl)(aryl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones 28 through asymmetric F–C reaction of indole 27 with 5-arylidene-2,2-dimethyl-1–3-dioxane-4–6-diones 26 . The developed synthetic protocol utilizes the effective catalyst L8 , affording the corresponding products in quantitative yield but with moderate enantiomeric ratios (up to 78:22 er; Scheme b).…”

Section: Conjugate Addition To Electrophilic Cc Bondsmentioning

confidence: 99%

“…In another study, Mocarska et al reported a series of thiourea-based organocatalysts for the preparation of chiral 5-((1 H -indol-3-yl)(aryl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones 28 through asymmetric F–C reaction of indole 27 with 5-arylidene-2,2-dimethyl-1–3-dioxane-4–6-diones 26 . 24 The developed synthetic protocol utilizes the effective catalyst L8 , affording the corresponding products in quantitative yield but with moderate enantiomeric ratios (up to 78:22 er; Scheme 5 b). Moreover, the bulkier side chain in the catalyst, such as the tert -butyl group, appeared to increase the effectiveness of the catalyst.…”

Section: Conjugate Addition To Electrophilic C=c Bondsmentioning

confidence: 99%

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Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

2022

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Functionalized chiral indole derivatives are privileged and versatile organic frameworks encountered in numerous pharmaceutically active agents and biologically active natural products. The catalytic asymmetric Friedel–Crafts reaction of indoles, catalyzed by chiral metal complexes or chiral organocatalysts, is one of the most powerful and atom-economical approaches to access optically active indole derivatives. Consequently, a wide range of electrophilic partners including α,β-unsaturated ketones, esters, amides, imines, β,γ-unsaturated α-keto- and α-ketiminoesters, ketimines, nitroalkenes, and many others have been successfully employed to achieve a plethora of functionalized chiral indole moieties. In particular, strategies for C–H functionalization in the phenyl of indoles require incorporation of a directing or blocking group in the phenyl or azole ring of indole. The discovery of chiral catalysts which can control enantiodiscrimination has gained a great deal of attention in recent years. This review will provide an updated account on the application of the asymmetric Friedel–Crafts reaction of indoles in the synthesis of diverse chiral indole derivatives, covering the timeframe from 2011 to today.

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Section: Conjugate Addition To Electrophilic C�c Bondsmentioning

confidence: 99%

Section: Conjugate Addition To Electrophilic Cc Bondsmentioning

confidence: 99%

Section: Conjugate Addition To Electrophilic C=c Bondsmentioning

confidence: 99%

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Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

2022

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“…Nevertheless, stereoselective synthesis of 5-((1H-indol-3-yl)(aryl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones is possible with the application of thiourea organocatalysts. 41 In the next synthetic step compound, 6 should be converted into the desired 1-aryl-1,2-dihydrocyclopenta[b] indol-3(4H)-one (5). We should take into consideration the work of Fillion 42,43 describing intramolecular Friedel-Crafts acylation with Meldrum's acid derivatives catalysed by metal trifluoromethanesulphonates, where the aryl ring was activated with acyloxy groups.…”

Section: Synthesismentioning

confidence: 99%

Design, synthesis, and molecular docking of new 5-HT reuptake inhibitors based on modified 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold

et al. 2019

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A new group of serotonin reuptake inhibitors containing 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold was synthesized, starting from indole 5-((1H-indol-3-yl)(1,3-dioxane-4,6-diones as a key intermediates. Following three transformations including intramolecular cyclization and formation of imines, a series of new ligand for human serotonin transporter was obtained. The ability of these ligands to inhibit human TS3 serotonin transporter as well as selectivity toward human D3 dopamine receptor and dopamine transporter were tested in silico using docking software.

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Multicomponent Catalytic Enantioselective Synthesis of Isoxazolidin‐5‐Ones

et al. 2021

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We report herein a strategy to afford a multicomponent catalytic enantioselective synthesis of β‐substituted isoxazolidin‐5‐ones via a KMC process promoted by a suited cupreine used as bifunctional organocatalyst. The hydroxamic acid component, with a sterically hindered amide moiety, proved to be key for the successful formation and transformation of the obtained original N‐amide isoxazolidin‐5‐ones.

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New thiourea organocatalysts and their application for the synthesis of 5-(1H-indol-3-yl)methyl-2,2-dimethyl-1,3-dioxane-4,6-diones a source of chiral 3-indoylmethyl ketenes

Cited by 6 publications

References 16 publications

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

Design, synthesis, and molecular docking of new 5-HT reuptake inhibitors based on modified 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold

Multicomponent Catalytic Enantioselective Synthesis of Isoxazolidin‐5‐Ones

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