Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols.
A variety of routes are described for the synthesis of a-silyloxy aldehydes in which the silicon atom bears a prenyl side chain. These compounds are shown to undergo stereoselective carbonyl ene cyclisation under mildly Lewis acidic conditions and the derived silacycles are cleaved to afford single...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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2003
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| _version_ | 1797094050406334464 |
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| author | Robertson, J Hall, M Stafford, P Green, S |
| author_facet | Robertson, J Hall, M Stafford, P Green, S |
| author_sort | Robertson, J |
| collection | OXFORD |
| description | A variety of routes are described for the synthesis of a-silyloxy aldehydes in which the silicon atom bears a prenyl side chain. These compounds are shown to undergo stereoselective carbonyl ene cyclisation under mildly Lewis acidic conditions and the derived silacycles are cleaved to afford single diastereomers of functionalised triols. |
| first_indexed | 2024-03-07T04:08:45Z |
| format | Journal article |
| id | oxford-uuid:c718e6aa-56c0-47b3-9bbf-b23e8d71c6c0 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:08:45Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:c718e6aa-56c0-47b3-9bbf-b23e8d71c6c02022-03-27T06:42:39ZEne cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c718e6aa-56c0-47b3-9bbf-b23e8d71c6c0EnglishSymplectic Elements at Oxford2003Robertson, JHall, MStafford, PGreen, SA variety of routes are described for the synthesis of a-silyloxy aldehydes in which the silicon atom bears a prenyl side chain. These compounds are shown to undergo stereoselective carbonyl ene cyclisation under mildly Lewis acidic conditions and the derived silacycles are cleaved to afford single diastereomers of functionalised triols. |
| spellingShingle | Robertson, J Hall, M Stafford, P Green, S Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title | Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title_full | Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title_fullStr | Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title_full_unstemmed | Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title_short | Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols. |
| title_sort | ene cyclisations of alpha prenyl dialkylsilyloxy aldehydes formation and oxidative cleavage of oxasilacyclohexanols |
| work_keys_str_mv | AT robertsonj enecyclisationsofalphaprenyldialkylsilyloxyaldehydesformationandoxidativecleavageofoxasilacyclohexanols AT hallm enecyclisationsofalphaprenyldialkylsilyloxyaldehydesformationandoxidativecleavageofoxasilacyclohexanols AT staffordp enecyclisationsofalphaprenyldialkylsilyloxyaldehydesformationandoxidativecleavageofoxasilacyclohexanols AT greens enecyclisationsofalphaprenyldialkylsilyloxyaldehydesformationandoxidativecleavageofoxasilacyclohexanols |