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A Short Sequence for the Iterative Synthesis of Fused Polyethers
Author(s) -
Elustondo Frédéric,
Chintalapudi Venkaiah,
Clark J. Stephen
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900161
Subject(s) - chemistry , alkene , hydroboration , ring closing metathesis , metathesis , sequence (biology) , ozonolysis , ether , silane , williamson ether synthesis , acyclic diene metathesis , ring (chemistry) , salt metathesis reaction , synthon , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , polymer , polymerization
Abstract 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.