A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress...
| Published in: | Beilstein Journal of Organic Chemistry |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2011-06-01
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| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.7.91 |
| _version_ | 1852732281241731072 |
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| author | Berenger Biannic Thomas Ghebreghiorgis Aaron Aponick |
| author_facet | Berenger Biannic Thomas Ghebreghiorgis Aaron Aponick |
| author_sort | Berenger Biannic |
| collection | DOAJ |
| container_title | Beilstein Journal of Organic Chemistry |
| description | The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPureTM MPA is an efficient scavenging reagent that halts the reaction progress. |
| format | Article |
| id | doaj-art-8d4e807e7c79470f907fbf8b6fe7e2a3 |
| institution | Directory of Open Access Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2011-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| spelling | doaj-art-8d4e807e7c79470f907fbf8b6fe7e2a32025-08-19T21:08:05ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-06-017180280710.3762/bjoc.7.911860-5397-7-91A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethersBerenger Biannic0Thomas Ghebreghiorgis1Aaron Aponick2Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, U.S.ADepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, U.S.ADepartment of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, U.S.AThe Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPureTM MPA is an efficient scavenging reagent that halts the reaction progress.https://doi.org/10.3762/bjoc.7.91allylic alcoholallylic etherAu-catalyzedSN2'tetrahydropyran |
| spellingShingle | Berenger Biannic Thomas Ghebreghiorgis Aaron Aponick A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers allylic alcohol allylic ether Au-catalyzed SN2' tetrahydropyran |
| title | A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers |
| title_full | A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers |
| title_fullStr | A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers |
| title_full_unstemmed | A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers |
| title_short | A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers |
| title_sort | comparative study of the au catalyzed cyclization of hydroxy substituted allylic alcohols and ethers |
| topic | allylic alcohol allylic ether Au-catalyzed SN2' tetrahydropyran |
| url | https://doi.org/10.3762/bjoc.7.91 |
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