| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5221050 | Tetrahedron | 2012 | 6 Pages |
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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Boris A. Trofimov, Elena Yu. Schmidt, Ivan A. Bidusenko, Igor' A. Ushakov, Nadezhda I. Protsuk, Nadezhda V. Zorina, Albina I. Mikhaleva,