NMR chiral discrimination of chalcogen containing secondary alcohols

Marques, Naiade B.G.; Jacob, Raquel G.; Perin, Gelson; Lenardão, Eder J.; Silva, Márcio S.

doi:10.1002/chir.23030

Cited by 8 publications

(4 citation statements)

References 27 publications

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“…The solvent was evaporated under vacuum and the crude product was purified on silica gel to yield β-phenylseleno alcohols 8a,b. Spectroscopic data of compounds 8a [59] and 8b [47,60] matched those previously reported in the literature. ).…”

Section: Synthesis Of 33'-diselanediylbis(1-(benzyloxy)propan-2-ol) 7asupporting

confidence: 81%

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Synthesis of functionalised organochalcogenides and in vitro evaluation of their antioxidant activity

Capperucci

Coronnello

Salvini

et al. 2021

Bioorganic Chemistry

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Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70 th birthdayThe antioxidant properties and the cytotoxicity of differently substituted β-hydroxyand β-amino dialkyl and alkyl-aryl tellurides, prepared through ring-opening reactions of epoxides and aziridines with selenium-or tellurium-centered nucleophiles, have been investigated on normal human dermal fibroblasts. Most of the studied compounds exhibited a low cytotoxicity and a number of them proved to be non-toxic, not showing any effect on cell viability even at the highest concentration used (100 μM). The obtained results showed a significant antioxidant potential of the selected organotellurium compounds, particularly evident under conditions of exogenously induced oxidative stress. The antioxidant activity of selenium-containing analogues of active tellurides has also been evaluated on cells, highlighting that the replacement of Se with Te brought about a significant increase in the peroxidase activity.

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Section: Synthesis Of 33'-diselanediylbis(1-(benzyloxy)propan-2-ol) 7asupporting

confidence: 81%

“…4.1.5. Synthesis of 1-(phenyltellanyl)propan-2-ol 3a [59] Following the general procedure, diphenyl ditelluride (51 mg, 0.125 mmol) and 2-methyloxirane (14 mg, 0.23 mmol) gave after flash chromatography (petroleum ether/EtOAc 3:1) 3a (55 mg, 91%).…”

Section: 14mentioning

confidence: 99%

Synthesis of functionalised organochalcogenides and in vitro evaluation of their antioxidant activity

Capperucci

Coronnello

Salvini

et al. 2021

Bioorganic Chemistry

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“…When the liquid crystal is chiral, solute−solvent interactions are diastereoselective, and the anisotropic NMR spectra of each enantiomer are consequently different. 986 In the last few years, Silva's group studied the enantiodifferentiation of chalcogen containing amines 987 and alcohols 988 by using 77 Se and 125 Te NMR spectroscopy, and the diastereomeric environment is provided by enantiopure derivatizing agents in both cases. The use of chalcogen ( 77 Se and 125 Te) NMR spectroscopy in chiral recognition is still in its infancy compared to other nuclides such as 19 F and 31 P. 958 The main advantage of chalcogen nuclides is their ability to detect different structures without the difficulties encountered in 1 H NMR, like overlapping signals, multiplicity, and high sensitivity to the analysis conditions.…”

Section: Enantioselective Sensingmentioning

confidence: 99%

“…In the last few years, Silva’s group studied the enantiodifferentiation of chalcogen containing amines and alcohols by using 77 Se and 125 Te NMR spectroscopy, and the diastereomeric environment is provided by enantiopure derivatizing agents in both cases. The use of chalcogen ( 77 Se and 125 Te) NMR spectroscopy in chiral recognition is still in its infancy compared to other nuclides such as 19 F and 31 P .…”

Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

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The on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)‐promoted reduction of elemental tellurium, reacts with a wide variety of electrophiles, including strained heterocycles, haloalkanes, Michael acceptors, and aryl diazonium salts, providing simple and rapid access to a broad range of novel functionalised symmetrical tellurides. The methodology well tolerated the presence of versatile functional groups such as alchohols, amines, esters, nitriles, and sulfones and allowed the incorporation of tellurium atoms into biologically relevant natural‐derived products. Furthermore, in the case of the nucleophilic ring opening of epoxides and aziridines, a judicious tuning of the reaction conditions enabled the synthesis of unreported β‐hydroxy‐ and β‐amino‐ditellurides, which were further employed as precursors of new functionalised unsymmetrical dialkyl tellurides. The thiol−peroxidase catalytic activity of hydroxy‐ditellurides has also been investigated in order to compare their antioxidant properties with those of homologous tellurides.

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NMR chiral discrimination of chalcogen containing secondary alcohols

Cited by 8 publications

References 27 publications

Synthesis of functionalised organochalcogenides and in vitro evaluation of their antioxidant activity

Synthesis of functionalised organochalcogenides and in vitro evaluation of their antioxidant activity

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

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