Title of article
A peculiar transition-metal-free cyclodimerization of propargylic alcohols to vinyl bicyclic ketals
Author/Authors
Boris A. Trofimov، نويسنده , , Elena Yu Schmidt، نويسنده , , Ivan A. Bidusenko، نويسنده , , Igorʹ A. Ushakov، نويسنده , , Nadezhda I. Protsuk، نويسنده , , Nadezhda V. Zorina، نويسنده , , Albina I. Mikhaleva، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
6
From page
1241
To page
1246
Abstract
Propargylic alcohols, alkylaryl(hetaryl)ethynyl carbinols, under transition-metal-free conditions (KOH/DMSO, 70–80 °C, 10–15 min) unexpectedly undergo stereoselective cyclodimerization to 7-methylene-6,8-dioxabicyclo[3.2.1]octanes having the scaffold of known insect pheromones and marine toxins. Under acetylenic pressure the yields of bicyclic ketals reach 80%. In all the cases, the cyclodimers are formed exclusively as one diastereomer.
Keywords
Acetylenic alcohols , Acetylene , Super base , 6
Journal title
Tetrahedron
Serial Year
2012
Journal title
Tetrahedron
Record number
1104158
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