Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols.
A highly efficient gold-catalyzed cycloisomerization reaction of bis-homopropargylic diols is described. The cyclizations are conducted in the presence of either AuI or AuIII catalysts in MeOH at room temperature in a very short time. The reaction conditions are compatible with functional groups, such as n-butyl, phenyl, allyl, benzyl, and alcohol groups, leading to original strained dioxabicyclo[2.2.1], -[2.2.2], or -[3.2.1] ketals in good to excellent yields.
Antoniotti
Sylvain
S
Laboratoire de Synthèse Sélective Organique et Produits Naturels, E.N.S.C.P., UMR 7573, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
Genin
Emilie
E
Michelet
Véronique
V
Genêt
Jean-Pierre
JP