Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol
An organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two...
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MDPI AG
2024-08-01
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| Online Access: | https://www.mdpi.com/1422-8599/2024/3/M1867 |
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| author | Anna Esposito Annalisa Guaragna |
| author_facet | Anna Esposito Annalisa Guaragna |
| author_sort | Anna Esposito |
| collection | DOAJ |
| description | An organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two double bonds masked by two dithiodimethylene bridges that can be stereoselectively removed to give a <i>E</i>,<i>E</i>- or <i>Z</i>,<i>Z</i>-configured divinylcarbinol. These products could then be conveniently functionalized, for example, with hydroxyl or amino functions, for the construction of the skeleton of more complex systems. |
| format | Article |
| id | doaj-art-5b9601db4b284fec9d1d2669ce43c541 |
| institution | OA Journals |
| issn | 1422-8599 |
| language | English |
| publishDate | 2024-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-5b9601db4b284fec9d1d2669ce43c5412025-08-20T01:55:42ZengMDPI AGMolbank1422-85992024-08-0120243M186710.3390/M1867Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanolAnna Esposito0Annalisa Guaragna1Department of Chemical, Materials and Production Engineering, University of Naples Federico II, I-80125 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, I-80126 Naples, ItalyAn organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two double bonds masked by two dithiodimethylene bridges that can be stereoselectively removed to give a <i>E</i>,<i>E</i>- or <i>Z</i>,<i>Z</i>-configured divinylcarbinol. These products could then be conveniently functionalized, for example, with hydroxyl or amino functions, for the construction of the skeleton of more complex systems.https://www.mdpi.com/1422-8599/2024/3/M1867homologating agentdithiinsdivinylcarbinoltandem processorganolithium compounds |
| spellingShingle | Anna Esposito Annalisa Guaragna Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol Molbank homologating agent dithiins divinylcarbinol tandem process organolithium compounds |
| title | Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol |
| title_full | Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol |
| title_fullStr | Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol |
| title_full_unstemmed | Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol |
| title_short | Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol |
| title_sort | bis 3 4 methoxybenzyl oxy methyl 5 6 dihydro 1 4 dithiin 2 yl methanol |
| topic | homologating agent dithiins divinylcarbinol tandem process organolithium compounds |
| url | https://www.mdpi.com/1422-8599/2024/3/M1867 |
| work_keys_str_mv | AT annaesposito bis34methoxybenzyloxymethyl56dihydro14dithiin2ylmethanol AT annalisaguaragna bis34methoxybenzyloxymethyl56dihydro14dithiin2ylmethanol |