Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination
The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.85 |
| _version_ | 1828917815086678016 |
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| author | Łukasz Górecki Artur Mucha Paweł Kafarski |
| author_facet | Łukasz Górecki Artur Mucha Paweł Kafarski |
| author_sort | Łukasz Górecki |
| collection | DOAJ |
| description | The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates, first reported compounds containing a direct P–C bond between the quinine carbon skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced. |
| first_indexed | 2024-12-13T20:58:15Z |
| format | Article |
| id | doaj.art-59cfbbf0e447475cbaff32665b368428 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T20:58:15Z |
| publishDate | 2014-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-59cfbbf0e447475cbaff32665b3684282022-12-21T23:31:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110188388910.3762/bjoc.10.851860-5397-10-85Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine eliminationŁukasz Górecki0Artur Mucha1Paweł Kafarski2Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandThe Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates, first reported compounds containing a direct P–C bond between the quinine carbon skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced.https://doi.org/10.3762/bjoc.10.85carbonyl derivativesdialkyl phosphite additionorganophosporusphosphonate–phosphate rearrangementquinine oxidation |
| spellingShingle | Łukasz Górecki Artur Mucha Paweł Kafarski Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination Beilstein Journal of Organic Chemistry carbonyl derivatives dialkyl phosphite addition organophosporus phosphonate–phosphate rearrangement quinine oxidation |
| title | Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination |
| title_full | Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination |
| title_fullStr | Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination |
| title_full_unstemmed | Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination |
| title_short | Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination |
| title_sort | addition of h phosphonates to quinine derived carbonyl compounds an unexpected c9 phosphonate phosphate rearrangement and tandem intramolecular piperidine elimination |
| topic | carbonyl derivatives dialkyl phosphite addition organophosporus phosphonate–phosphate rearrangement quinine oxidation |
| url | https://doi.org/10.3762/bjoc.10.85 |
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