Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols
The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in cyclization and the formation of 3-hydroxy tetrahydrofurans (56–85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66–83%) and the cyclization product in po...
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2016
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| Online Access: | http://dx.doi.org.access.msu.ac.zw:2048/10.1016/j.tetlet.2012.08.110 |
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| author | Makhosazana, P. Gamedze, Rejoice Maseko, B Chigondo, Fidelis Nkambule, Comfort, M. |
| author_facet | Makhosazana, P. Gamedze, Rejoice Maseko, B Chigondo, Fidelis Nkambule, Comfort, M. |
| author_sort | Makhosazana, P. |
| collection | DSpace |
| description | The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in
cyclization and the formation of 3-hydroxy tetrahydrofurans (56–85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66–83%) and the cyclization product in poor yield (5– 12%). A mechanism that justifies these observations is proposed to occur via the tosylation of the primary hydroxyl followed by an intramolecular tin acetal rearrangement to a 1,3-stannylene which then undergoes a 5-exo-tet-cyclization. The difference in rates of cyclization reactivity is due to the energetically more stable tin acetals of syn-1,3-diols compared to those of anti-1,3-diols. |
| format | Article |
| id | ir-11408-1067 |
| institution | My University |
| language | English |
| publishDate | 2016 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | ir-11408-10672022-06-27T13:49:06Z Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols Makhosazana, P. Gamedze, Rejoice Maseko, B Chigondo, Fidelis Nkambule, Comfort, M. Sulfonylation Tin acetal 1,2,4-Triols, 1,3-Diols Tetrahydrofurans The reaction of syn-1,2,4-triols under sulfonylation conditions catalyzed by Bu2SnO (5 mol %) results in cyclization and the formation of 3-hydroxy tetrahydrofurans (56–85%) while the anti-1,2,4-triols react to give C1-O-sulfonyl derivatives in good yields (66–83%) and the cyclization product in poor yield (5– 12%). A mechanism that justifies these observations is proposed to occur via the tosylation of the primary hydroxyl followed by an intramolecular tin acetal rearrangement to a 1,3-stannylene which then undergoes a 5-exo-tet-cyclization. The difference in rates of cyclization reactivity is due to the energetically more stable tin acetals of syn-1,3-diols compared to those of anti-1,3-diols. 2016-04-26T16:45:58Z 2016-04-26T16:45:58Z 2012 Article 0040-4039 http://dx.doi.org.access.msu.ac.zw:2048/10.1016/j.tetlet.2012.08.110 en Tetrahedron Letters;Vol. 53, p. 5929–5932 none Elsevier |
| spellingShingle | Sulfonylation Tin acetal 1,2,4-Triols, 1,3-Diols Tetrahydrofurans Makhosazana, P. Gamedze, Rejoice Maseko, B Chigondo, Fidelis Nkambule, Comfort, M. Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title_full | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title_fullStr | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title_full_unstemmed | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title_short | Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| title_sort | serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols |
| topic | Sulfonylation Tin acetal 1,2,4-Triols, 1,3-Diols Tetrahydrofurans |
| url | http://dx.doi.org.access.msu.ac.zw:2048/10.1016/j.tetlet.2012.08.110 |
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