Synthesis of 1,7-dioxaspiro[5.5]undecanes and 1-oxa-7-thiaspiro[5.5]undecanes from exo-glycal
作者:Hui-Chang Lin、Yen-Bo Chen、Zi-Ping Lin、Fung Fuh Wong、Chun-Hung Lin、Shao-Kai Lin
DOI:10.1016/j.tet.2010.04.075
日期:2010.7
A new spirocyclization was developed for the synthesis of 1,7-dioxaspiro[5.5]undecanes and 1-oxa-7-thiaspiro[5.5]undecanes by reaction of exo-glycal with aryl alcohols or thiophenols in the presence of Lewis acid BF3·OEt2. The reaction proceeded through tandem Ferrier rearrangement, glycosylation, and Friedel–Crafts alkylation to provide the corresponding products in good to excellent yields.