Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes
Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products....
| Hauptverfasser: | , , , , |
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| Format: | Journal article |
| Sprache: | English |
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Wiley
2014
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| _version_ | 1826279331415982080 |
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| author | Elbert, B Lim, D Gudmundsson, H O'Hanlon, J Anderson, E |
| author_facet | Elbert, B Lim, D Gudmundsson, H O'Hanlon, J Anderson, E |
| author_sort | Elbert, B |
| collection | OXFORD |
| description | Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif. © 2014 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim. |
| first_indexed | 2024-03-06T23:57:06Z |
| format | Journal article |
| id | oxford-uuid:749cb773-3e3b-42db-b7a8-3155a78f7be6 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T23:57:06Z |
| publishDate | 2014 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:749cb773-3e3b-42db-b7a8-3155a78f7be62022-03-26T20:04:05ZSynthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:749cb773-3e3b-42db-b7a8-3155a78f7be6EnglishSymplectic Elements at OxfordWiley2014Elbert, BLim, DGudmundsson, HO'Hanlon, JAnderson, ECyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif. © 2014 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim. |
| spellingShingle | Elbert, B Lim, D Gudmundsson, H O'Hanlon, J Anderson, E Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title | Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title_full | Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title_fullStr | Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title_full_unstemmed | Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title_short | Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes |
| title_sort | synthesis of cyclic alkenylsiloxanes by semihydrogenation a stereospecific route to z alkenyl polyenes |
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