Regioselectivity of Mercury-Promoted Oxacyclizations of Alkynyl Diols

Abstract Hg(OTf) 2 -catalyzed cyclization of an alkynyl alcohol on a tetra­hydropyran template gives the bispyranyl ketone arising from dehydrative cyclization and alkyne hydration, rather than the targeted fused pyran-oxepane product. The combination of stoichiometric Hg(OTf) 2 and triethylsilane g...

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Bibliographic Details
Published in:Synlett 2017-12, Vol.28 (20), p.2951-2955
Main Authors: Hurtak, Jessica A., McDonald, Frank E.
Format: Article
Language:English
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Summary:Abstract Hg(OTf) 2 -catalyzed cyclization of an alkynyl alcohol on a tetra­hydropyran template gives the bispyranyl ketone arising from dehydrative cyclization and alkyne hydration, rather than the targeted fused pyran-oxepane product. The combination of stoichiometric Hg(OTf) 2 and triethylsilane gives reductive cyclization, but affords the fused pyran-oxocane corresponding to an 8- endo -mode oxacyclization process.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588562