Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones
The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluor...
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/4/6153 |
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| author | Hannah J. Edwards Sean Goggins Christopher G. Frost |
| author_facet | Hannah J. Edwards Sean Goggins Christopher G. Frost |
| author_sort | Hannah J. Edwards |
| collection | DOAJ |
| description | The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using commercially-available [Rh(cod)(OH)]2 catalyst. The selective formation of the 2,6-trans-tetrahydropyran stereoisomer is consistent with a mechanism involving alkene association and carbometalation on the less hindered face of the dihydropyranone. |
| first_indexed | 2024-12-24T13:05:44Z |
| format | Article |
| id | doaj.art-847504fc76054d5a9280d840c831c71c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-24T13:05:44Z |
| publishDate | 2015-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-847504fc76054d5a9280d840c831c71c2022-12-21T16:54:00ZengMDPI AGMolecules1420-30492015-04-012046153616610.3390/molecules20046153molecules20046153Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to DihydropyranonesHannah J. Edwards0Sean Goggins1Christopher G. Frost2Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UKDepartment of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UKDepartment of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UKThe selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using commercially-available [Rh(cod)(OH)]2 catalyst. The selective formation of the 2,6-trans-tetrahydropyran stereoisomer is consistent with a mechanism involving alkene association and carbometalation on the less hindered face of the dihydropyranone.http://www.mdpi.com/1420-3049/20/4/6153boronic acidsconjugate additionrhodiumtetrahydropyran |
| spellingShingle | Hannah J. Edwards Sean Goggins Christopher G. Frost Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones Molecules boronic acids conjugate addition rhodium tetrahydropyran |
| title | Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones |
| title_full | Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones |
| title_fullStr | Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones |
| title_full_unstemmed | Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones |
| title_short | Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones |
| title_sort | trans selective rhodium catalysed conjugate addition of organoboron reagents to dihydropyranones |
| topic | boronic acids conjugate addition rhodium tetrahydropyran |
| url | http://www.mdpi.com/1420-3049/20/4/6153 |
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