Synlett
DOI: 10.1055/s-0036-1588562
letter
© Georg Thieme Verlag Stuttgart · New York

Regioselectivity of Mercury-Promoted Oxacyclizations of Alkynyl Diols

Jessica A. Hurtak, Frank E. McDonald*
This material is based upon work supported by the National Science Foundation under CHE-1362249. We also acknowledge the Bruker AVANCE III HD 600 MHz NMR spectrometer, supported by NSF grant CHE-1531620
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Publication History

Received: 22 June 2017

Accepted after revision: 28 July 2017

Publication Date:
23 August 2017 (eFirst)

Dedicated in celebration of the 80th birthday of Professor Victor Snieckus

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.

Supporting Information