Mechanistic Studies on the Organocatalytic α‐Chlorination of Aldehydes: The Role and Nature of Off‐Cycle Intermediates

Ponath, Sebastian; Menger, Martina; Grothues, Lydia; Weber, Manuela; Lentz, Dieter; Strohmann, Carsten; Christmann, Mathias

doi:10.1002/ange.201806261

Cited by 5 publications

(2 citation statements)

References 37 publications

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“…The structural analogues of the studied compounds are present in the CCDC, e.g., SUXXAN [32], FIWJOK [33], NAWKOO [34], ZOZTIR [35], WOVTAF [36], and XUPLIG [37] for 1R or 2R and PAGTUM [38], KETFAM [39], and KEPQAB [8] for 2A. The comparison of SUXXAN against 1R and 2R (Figure 5) shows a conserved molecular geometry for the 1-(dimethylamino)propan-2-one and 1-(methylamino)propan-2-one tails linked to the adamantane.…”

Section: Single-crystal Analysesmentioning

confidence: 99%

Amantadine and Rimantadine Analogues—Single-Crystal Analysis and Anti-Coronaviral Activity

Shishkova,

Stoymirska,

Chayrov

et al. 2023

Crystals

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In this study, we utilized the human coronavirus 229E (HCoV-229E) for evaluating the in vitro efficacy of some analogues of the ion-channel inhibitors and Amantadine and Rimantadine. The application of these investigated compounds did not result in any detectable cytotoxic effects. Furthermore, we observed that the derivatives of both analogues did not affect the viability of MDBK cells. Amantadine and Rimantadine applied at a concentration of 50 μg/mL inhibited the replication by 47% and 36%, respectively. The derivatives of Amantadine displayed a slightly weaker inhibitory effect in comparison with its own inhibitory effect. The derivative 4R of Rimantadine exhibited the same antiviral effect as the Rimantadine control, inhibiting viral replication by 37%. However, the other two derivatives of Rimantadine demonstrated lower activities. The molecular structures of the newly synthesized compounds were investigated thoroughly using single-crystal X-ray analysis. Molecular docking studies were performed using Autodock Vina. Two of the studied compounds 2A and 4A showed a promising binding affinity (−8.3 and −8.0 kcal/mol) towards SARS-CoV-2 RNA-dependent polymerase RNA site and SARS-CoV-2 Nsp3 (207-379, MES site) respectively.

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Section: Single-crystal Analysesmentioning

confidence: 99%

Amantadine and Rimantadine Analogues—Single-Crystal Analysis and Anti-Coronaviral Activity

Shishkova,

Stoymirska,

Chayrov

et al. 2023

Crystals

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“…Employing electron-rich chlorine source 11 at 10 °C gave 2α-chloro-sclareolide ( 10 ) in a yield of 41% within 100 min using a 3D-printed photoreactor (for details, see the Supporting Information). To prove scalability, this transformation was repeated on gram scale and gave a similar yield of 38%.…”

mentioning

confidence: 99%

A Modular, Argon-Driven Flow Platform for Natural Product Synthesis and Late-Stage Transformations

et al. 2021

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A modular flow platform for the synthesis of natural products and their analogs was designed. To access different reaction setups with a maximum of flexibility, interchangeable 3D-printed components serve as backbone. By switching from conventional liquid-to gas-driven flow, reagent and solvent waste is minimized which translates into an advantageous sustainability and economy profile. To enable inert conditions, practical "Schlenk-in-flow" techniques for the safe handling of oxygen-and moisture sensitive reagents were developed. Adopting these techniques, reproducible transformations in natural product synthesis were achieved. File list (2) download file view on ChemRxiv manuscript_Heretsch_CA.pdf (585.79 KiB) download file view on ChemRxiv SI_Heretsch.pdf (7.03 MiB)

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Der Aufstieg der Trichloride Ermöglicht eine Verbesserte Chlortechnologie

Kleoff¹,

Voßnacker²,

Hasenstab-Riedel³

2023

Angewandte Chemie

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Chlor spielt eine zentrale Rolle bei der industriellen Herstellung zahlreicher Produkte von globaler Bedeutung. In jüngster Zeit haben sich Polychloride von einem Gebiet akademischen Interesses zu einem Forschungsthema mit enormem industriellen Potenzial entwickelt. In diesem Aufsatz wird der Wert von Trichloriden für die Chlorspeicherung und Chlorierungsreaktionen skizziert. Insbesondere die kostengünstige ionische Flüssigkeit [NEt3Me][Cl3] zeigt eine ähnliche und manchmal sogar vorteilhafte Reaktivität im Vergleich zu Chlorgas und bietet gleichzeitig ein besseres Sicherheitsprofil. Als Chlorspeicher eingesetzt, könnte [NEt3Me][Cl3] dazu beitragen, die derzeitigen Einschränkungen bei der Lagerung und dem Transport von Chlor in größeren Mengen zu überwinden. So könnten Trichloride zu einer Schlüsseltechnik für die Flexibilisierung der Chlorproduktion werden, die eine Nutzung erneuerbarer, aber schwankender elektrischer Energie ermöglicht. Da es sich bei dem geladenen Speicher, [NEt3Me][Cl3], um ein bewährtes Chlorierungsreagenz handelt, könnte es direkt für nachgelagerte Prozesse eingesetzt werden und den Weg zu einer praktischeren und sichereren Chlorindustrie ebnen.

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Mechanistic Studies on the Organocatalytic α‐Chlorination of Aldehydes: The Role and Nature of Off‐Cycle Intermediates

Abstract: Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

Cited by 5 publications

References 37 publications

Amantadine and Rimantadine Analogues—Single-Crystal Analysis and Anti-Coronaviral Activity

Amantadine and Rimantadine Analogues—Single-Crystal Analysis and Anti-Coronaviral Activity

A Modular, Argon-Driven Flow Platform for Natural Product Synthesis and Late-Stage Transformations

Der Aufstieg der Trichloride Ermöglicht eine Verbesserte Chlortechnologie

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