Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides

Sokolov, A. Yu.; Golovach, S. M.; Kozlinsky, Ihor; Dolia, Krystyna; Tolmachev, Andrey A.; Kuchkovska, Yuliya O.; Grygorenko, Oleksandr O.

doi:10.1055/s-0037-1611277

Cited by 3 publications

(2 citation statements)

References 40 publications

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“…The authors have cited additional references within the Supporting Information. [34][35][36][37][38][39][40][41][42][43][44][45][46][47]…”

Section: Supporting Informationmentioning

confidence: 99%

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Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis

Groslambert,

Pale,

Mamane

2024

Chemistry A European J

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The ability of triaryltelluronium salts to interact with N‐halosuccinimides (NXS) through chalcogen bonding (ChB) in the solid state and in solution is demonstrated herein. Cocrystals of the triaryltelluronium bearing two CF3 electron‐withdrawing groups per aryl ring with N‐chloro‐, N‐bromo‐ and N‐iodosuccinimide (respectively NCS, NBS and NIS) were analyzed by X‐ray diffraction, evidencing a ChB between tellurium and the carbonyl group of NXS. This ChB was confirmed in solution by NMR spectroscopy, especially by 125Te NMR titration experiment, which allowed the determination of the association constant (Ka) between the telluronium and NBS. The so‐obtained Ka value of 17.3 ± 0.6 M‐1 indicated a moderate interaction in solution because of the competitive role of the solvent. The strength of the Te‐‐‐O ChB was however sufficient enough to promote the catalytic halofunctionalization of aromatics and of alkenes such as the intra‐ and intermolecular haloalkoxylation and haloesterification of alkenes.

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“…The authors have cited additional references within the Supporting Information. [34][35][36][37][38][39][40][41][42][43][44][45][46][47]…”

Section: Supporting Informationmentioning

confidence: 99%

“…X‐ray diffraction data of cocrystals, NMR spectroscopy details (chemical shift variation data and titration experiments) and full details on catalysis experiments are available in the Supporting Information. The authors have cited additional references within the Supporting Information [34–47] …”

Section: Supporting Informationmentioning

confidence: 99%

Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis

Groslambert,

Pale,

Mamane

2024

Chemistry A European J

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Synthesis and reactions of ω-CF3O-substituted aliphatic sulfonyl chlorides

Logvinenko

Kondratov

Dobrydnev

et al. 2021

Journal of Fluorine Chemistry

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A Close-up Look at the Chemical Space of Commercially Available Building Blocks for Medicinal Chemistry

Zabolotna

Volochnyuk

Ryabukhin

et al. 2021

J. Chem. Inf. Model.

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The ability to efficiently synthesize desired compounds can be a limiting factor for chemical space exploration in drug discovery. This ability is conditioned not only by the existence of well-studied synthetic protocols but also by the availability of corresponding reagents, so-called building blocks (BB). In this work, we present a detailed analysis of the chemical space of 400K purchasable BB. The chemical space was defined by corresponding synthons -fragments contributed to the final molecules upon reaction. They allow an analysis of BB physicochemical properties and diversity, unbiased by the leaving and protective groups in actual reagents. The main classes of BB were analyzed in terms of their availability, rule-of-two-defined quality, and diversity. Available BBs were eventually compared to a reference set of biologically relevant synthons derived from ChEMBL fragmentation, in order to illustrate how well they cover the actual medicinal chemistry needs. This was performed on a newly constructed universal generative topographic map of synthon chemical space, allowing to visualize both libraries and analyze their overlapping and library-specific regions.

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Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides

Cited by 3 publications

References 40 publications

Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis

Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis

Synthesis and reactions of ω-CF3O-substituted aliphatic sulfonyl chlorides

A Close-up Look at the Chemical Space of Commercially Available Building Blocks for Medicinal Chemistry

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