Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems

Abstract : (Chemical Equation Presented) 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 SN2' process affording 1,6- and 1,4-dioxygenated derivatives, respectively.
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F.-D. Boyer, Issam Hanna. Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems. Journal of Organic Chemistry, American Chemical Society, 2005, 70 (3), pp.1077-1080. ⟨10.1021/jo0481295⟩. ⟨hal-00954807⟩

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