1,4-dioxene in organic synthesis: rapid access to the oxabicyclo
[formula: see text] Oxidation of 2,3-disubstituted 1,4-dioxenes 3 with m-chloroperbenzoic acid in methanol followed by nucleophilic addition of allyltrimethylsilane in the presence of TiCl4 afforded dienes 5, which have been converted to oxabicyclo[4.2.1] nonenes 8 in excellent yield by olefin ring-closing metathesis reaction.
Hanna
I
Laboratoire de Synthese Organique associe au CNRS, Ecole Polytechnique, Palaiseau, France. hanna@poly.polytechnique.fr
Michaut
V