A Short Sequence for the Iterative Synthesis of Fused Polyethers

A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent...

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Veröffentlicht in:Helvetica chimica acta 2019-09, Vol.102 (9), p.n/a
Hauptverfasser: Elustondo, Frédéric, Chintalapudi, Venkaiah, Clark, J. Stephen
Format: Artikel
Sprache:eng
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Zusammenfassung:A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201900161