119336-33-3Relevant academic research and scientific papers
New one-step process for the synthesis of functionalized 1,6-dioxaspiro[4,5]decanes
Carretero, Juan C.,Rojo, Javier,Diaz, Nuria,Hamdouchi, Chafiq,Poveda, Ana
, p. 8507 - 8524 (2007/10/02)
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 it affords 1,6-dioxaspiro[4,5]decanes in good yields in one-step procedure. This new method of synthesis of spiroketals, in non-acid conditions, is thermodynamically controlled and occurs with high stereoselectivity at C-4, C-5 and C-7, but not at C-2.
