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A Highly Efficient Access to Spiroketals, Mono-unsaturated Spiroketals, and Furans: Hg(II)-Catalyzed Cyclization of Alkyne Diols and Triols

Kontham Ravindar, Maddi Sridhar Reddy and Pierre Deslongchamps*

*Département de chimie, Faculté des sciences et de génie, Pavillon Alexandre-Vachon, Université Laval, 1045, avenue de la Médecine, Québec (Québec) G1 V 0A6, Canada, Email: pierre.deslongchampschm.ulaval.ca

K. Ravindar, M. S. Reddy, P. Deslongchamps, Org. Lett., 2011, 13, 3178-3181.

DOI: 10.1021/ol201102x (free Supporting Information)


Abstract

Hg(II) salts are highly efficient catalysts for a versatile construction of spiroketals in an instant reaction in high yields at ambient temperature from alkyne diols or THP-semiprotected alkyne diols in aqueous conditions. Monounsaturated spiroketals and furans were accessed with equal ease when propargylic triols (or propargylic diols) were subjected to similar conditions.

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Key Words

Acetals, Lactols, Cyclization


ID: J54-Y2011-1740