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Studies on the intramolecular oxa-Pictet–Spengler rearrangement of 5-aryl-1,3-dioxolanes to 4-hydroxy-isochromans
| Content Provider | Semantic Scholar |
|---|---|
| Author | Bianchi, Darío A. Rúa, Federico De La Kaufman, Teodoro S. |
| Copyright Year | 2004 |
| Abstract | Abstract The success and stereochemical outcome of the TiCl 4 -promoted oxa-Pictet–Spengler cyclization of 5-aryl-1,3-dioxolanes to produce 1,3-disubstituted-4-hydroxy-isochromans, is influenced by the length and nature of the side chains bound to C-2 and C-4 of the dioxolane. Methyl groups yield a mixture of 4-hydroxy-isochromans in which the 1,3- trans diastereomer predominates, while bulkier substituents give 1,3- cis diastereomers. Functional groups in the C-2 side chain of the dioxolane ring may hinder cyclization by complexation with the promoter. |
| Starting Page | 411 |
| Ending Page | 415 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/j.tetlet.2003.10.143 |
| Volume Number | 45 |
| Alternate Webpage(s) | https://tk-team-iquir.webnode.com/_files/200000102-4c92d4e849/Tetrahedron%20Lett%202004%2045%20411.pdf |
| Alternate Webpage(s) | https://doi.org/10.1016/j.tetlet.2003.10.143 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
