Chirality transfer in the synthesis of 2,3-dihydro-1,4-dithiine derivatives

Depa, Wojciech J.; Buszta, Natalia; Guńka, Piotr A.; Zachara, Janusz; Bajek-Bil, Agata; Groszek, Grażyna

doi:10.1080/00397911.2020.1801746

Cited by 2 publications

(8 citation statements)

References 23 publications

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“…The structure of product 5 (crystallized from DCM) was confirmed by single-crystal X-ray diffraction (see Figure 1) in addition to full spectrometric analysis. 13 We obtained one diastereoisomer as a pair of enantiomers. The centrosymmetric crystal structure confirmed that it is a racemic mixture with 0% ee.…”

Section: Synlettmentioning

confidence: 99%

“…Column chromatography was performed on Merck silica gel 60 (230-400 mesh). NMR spectra were measured on a Bruker ADVANCE II 500 NMR spectrometer (500 MHz for 1 H spectra and 125 MHz for 13 C spectra), CDCl3 or TMS served as an internal standard. Chemical shifts (δ values) were quoted in parts per million (ppm), the following abbreviations were used to describe resonance signals splitting patterns when appropriate: s = singlet, d = doublet, dd = double of doubles, ddd = doublet of doublet doublet, dqd = doublet of doublet quartets, t = triplet, q = quartet, qd = a quartet of doubles, quin = pentet, m = multiplet, brs = broad singlet.…”

Section: General Informationmentioning

confidence: 99%

“…1,2-dithiepane, 11, as a colourless oil (33 mg; 25% yield) 1 H NMR (500 MHz, CDCl3):  = 2.84 (t, J 6.1, 4H, 2xSCH2); 2.05-2.00 (m, 4H, 2xSCH2CH2); 1.79-1.75 (m, 2H, SCH2CH2CH2). 13 C NMR (125 MHz, CDCl3):  = 39.5 (2C); 30.2 (2C); 26.2.…”

Section: Condensation Of Compounds 10mentioning

confidence: 99%

“…Crude product was purified by chromatography column (125fold silica gel excess, n-hexane:Et2O, 99:1) affording: Spectral data of the compound 12 are consistent with the literature. 13 This article is protected by copyright. All rights reserved.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…We predict that a dithioacetal with an unprotected hydroxyl group in the α position may be more prone to condensation reaction based on our previous results. 7…”

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confidence: 99%

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New Heterocyclic Organosulfur Compounds Derived from Dithioacetals

Groszek,

Leja,

Depa

et al. 2024

Synlett

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The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-; butane-1,4- and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric pair of enantiomers was obtained, the structure of which was confirmed by single-crystal X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis of complex chemical structures, macrocyclic compounds can be used to complex metal ions.

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Section: Synlettmentioning

confidence: 99%

Section: General Informationmentioning

confidence: 99%

Section: Condensation Of Compounds 10mentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

“…We predict that a dithioacetal with an unprotected hydroxyl group in the α position may be more prone to condensation reaction based on our previous results. 7…”

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confidence: 99%

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