Tetrahedron letters

Novel mercuric triflate-catalyzed condensation of ketones and homoallyl alcohols

M Nishizawa, T Shigaraki, H Takao, H Imagawa…

Index: Nishizawa; Shigaraki; Takao; Imagawa; Sugihara Tetrahedron Letters, 1999 , vol. 40, # 6 p. 1153 - 1156

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Citation Number: 22

Abstract

Novel condensation of ketones with homoallyl alcohols catalyzed by Hg (OTf) 2 has been developed, generating a 6-membered ring ether alcohol, bisether, and olefins. The reaction is initiated b hemiacetal formation, and cyclization of the resulting oxonium cation provides the 6-membered ring carbocation as a common intermediate. Thus, it is a catalytic Prins-type condensation of non-activated homoallyl alcohols and ordinary ketones.