Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

Borges, Elton L.; Peglow, Thiago J.; Silva, Márcio S.; Jacoby, Caroline Gross; Schneider, Paulo H.; Lenardão, Eder J.; Jacob, Raquel G.; Perin, Gelson

doi:10.1039/c5nj02945g

Cited by 11 publications

(7 citation statements)

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“…Neither variating the reaction temperature nor increasing the reaction time allowed to form Na 2 Te 2 . We also attempted to obtain Na 2 Te 2 through dismutation of Na 2 Te ( vide infra ) and elemental tellurium . However, albeit different conditions were evaluated, no reaction occurred and black unreacted tellurium was always observed.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

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“…The CDAs 1 a and 1 b were prepared according to our previously described synthetic route, using the ( S )‐solketal reagent as the starting material . The CDAs 1 a and 1 b were obtained in satisfactory yields after three steps (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Chalcogen‐Containing Diols: A Novel Chiral Derivatizing Agent for ⁷⁷Se and ¹²⁵Te NMR Chiral Recognition of Primary Amines

et al. 2019

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In this work, a novel chiral diol containing a chalcogen was developed for the 77Se and 125Te NMR chiral recognition of racemic primary amines. The enantiopure chiral derivatizing agents were synthesized from a readily available and versatile (S)‐solketal reagent. The synthesis was performed in three steps with satisfactory yields. The chiral derivatizing agents containing selenium or tellurium nuclides were evaluated for effective NMR chiral discrimination of racemic primary amines by a simple three component chiral derivatization protocol through the modified James‐Bull method. The split 77Se and 125Te NMR signals are well‐distinguishable and greater than 1H NMR signals. The Nuclear Overhauser Spectroscopy (NOESY) NMR 2D analysis and semi‐empirical method suggest a conformational preference of diastereoisomers, that provide information of the absolute configuration using selenium and tellurium chiral derivatizing agents.

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“…Still, the use of KF/Al 2 O 3 was studied as an alternative to prepare thioethers that allows the reuse of the solvent/catalytic system without previous treatment . More recently, our research group described the synthesis of enantiomerically pure bis(2,2‐dimethyl‐1,3‐dioxolanylmethyl) chalcogenides and dichalcogenides using the commercially available ( R )‐ and ( S )‐solketals …”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of 4‐Chalcogenylmethyl‐1,3‐dioxolan‐2‐ones and 1,3‐Bis(organylchalcogenyl)propan‐2‐ols from 3‐O‐Tosyl Glycerol 1,2‐Carbonate

et al. 2016

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We describe a selective method for synthesis of 4‐chalcogenylmethyl‐1,3‐dioxolan‐2‐ones and 1,3‐bis(organylchalcogenyl)propan‐2‐ols in a short reaction time through stoichiometric control. The use of 3‐O‐tosyl glycerol 1,2‐carbonate and a set of aryl and alkyl diorganyl dichalcogenides afforded the desired products in good to excellent yields. We also describe a synthetic application to 4‐chalcogenylmethyl‐1,3‐dioxolan‐2‐ones by base promoted the synthesis of 3‐(arylchalcogenyl)propane‐1,2‐diols in excellent yields.

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Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

Abstract: Enantiomerically pure bis-1,3-dioxolanylmethyl chalcogenides and dichalcogenides (S, Se and Te) were prepared from chalcogenides and chiral solketal tosylates.

Cited by 11 publications

References 47 publications

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Chalcogen‐Containing Diols: A Novel Chiral Derivatizing Agent for ⁷⁷Se and ¹²⁵Te NMR Chiral Recognition of Primary Amines

Selective Synthesis of 4‐Chalcogenylmethyl‐1,3‐dioxolan‐2‐ones and 1,3‐Bis(organylchalcogenyl)propan‐2‐ols from 3‐O‐Tosyl Glycerol 1,2‐Carbonate

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Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

Abstract: Enantiomerically pure bis-1,3-dioxolanylmethyl chalcogenides and dichalcogenides (S, Se and Te) were prepared from chalcogenides and chiral solketal tosylates.

Cited by 11 publications

References 47 publications

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Chalcogen‐Containing Diols: A Novel Chiral Derivatizing Agent for 77Se and 125Te NMR Chiral Recognition of Primary Amines

Selective Synthesis of 4‐Chalcogenylmethyl‐1,3‐dioxolan‐2‐ones and 1,3‐Bis(organylchalcogenyl)propan‐2‐ols from 3‐O‐Tosyl Glycerol 1,2‐Carbonate

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Chalcogen‐Containing Diols: A Novel Chiral Derivatizing Agent for ⁷⁷Se and ¹²⁵Te NMR Chiral Recognition of Primary Amines