Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems.
Acid-catalyzed addition of alcohols to tricyclic dienyl epoxides such as 4 or bicyclic vinyl oxiranes such as 17 exclusively occurred at the vinyl terminus of unsaturated system through a typical S(N)2' process affording 1,6- and 1,4-dioxygenated derivatives, respectively.
Boyer
François-Didier
FD
Unité de Phytopharmacie et Médiateurs Chimiques, INRA, Versailles, France.
Hanna
Issam
I