Tetrahedron

New one-step process for the synthesis of functionalized 1, 6-dioxaspiro [4, 5] decanes

JC Carretero, J Rojo, N Díaz, C Hamdouchi, A Poveda

Index: Carretero, Juan C.; Rojo, Javier; Diaz, Nuria; Hamdouchi, Chafiq; Poveda, Ana Tetrahedron, 1995 , vol. 51, # 31 p. 8507 - 8524

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Citation Number: 10

Abstract

β-Phenylsulfonyl dihydrofurans 1 were readily prepared by reduction of α-phenylsulfonyl-γ- lactones with DIBAL-H, followed by dehydration with MsCl-Et3N. Dihydrofurans 1 were deprotonated with n-BuLi and the resulting α-lithiated carbanion reacted with a wide variety of electrophiles. Particularly interesting is its reaction with γ-lactones because affords 1, 6- dioxaspiro [4, 5] decanes in good yields in one-step procedure. This new method of ...