The Journal of organic chemistry

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

FD Boyer, I Hanna

Index: Boyer, Francois-Didier; Hanna, Issam Journal of Organic Chemistry, 2005 , vol. 70, # 3 p. 1077 - 1080

Full Text: HTML

Citation Number: 13

Abstract

In an attempt to explore the effect of the ester group at C4, triene 14 11 was submitted to the above-described conditions. As in preceding examples, oxidation of 14 with m-CPBA at 0 °C in CH 2 Cl 2 and saturated aqueous NaHCO 3 was chemo- and stereoselective producing a mixture of two diastereomeric epoxides 15a and 15b as deduced from NMR spectra. However, treatment of the crude epoxide with allyl alcohol in the presence of catalytic Yb( ...