Title of article
Synthesis of 1,7-dioxaspiro[5.5]undecanes and 1-oxa-7-thiaspiro[5.5]undecanes from exo-glycal
Author/Authors
Hui-Chang Lin، نويسنده , , Yen-Bo Chen، نويسنده , , Zi-Ping Lin، نويسنده , , Fung Fuh Wong، نويسنده , , Chun-Hung Lin، نويسنده , , Shao-Kai Lin، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2010
Pages
6
From page
5229
To page
5234
Abstract
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.
Keywords
spirocyclization , Ferrier rearrangement , Friedel–Crafts alkylation , Spiroacetals
Journal title
Tetrahedron
Serial Year
2010
Journal title
Tetrahedron
Record number
1101021
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