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. T...
| Main Authors: | , , , , |
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| פורמט: | Journal article |
| שפה: | English |
| יצא לאור: |
2014
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| סיכום: | 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. |
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