Tetrahedron Letters p. 1153 - 1156 (1999)
Update date:2022-08-05
Topics:
Nishizawa
Shigaraki
Takao
Imagawa
Sugihara
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 by hemiacetal formation, and cyclization of the resulting oxonium action provides the 6-membered ring carbocation as a common intermediate. Thus, it is a catalytic Prins-type condensation of non-activated hormoallyl alcohols and ordinary ketones.
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