1,4-Dioxene in organic synthesis: Rapid access to the oxabicyclo[4.2.1]nonene system

Issam Hanna (1) , Valérie Michaut (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domaines: Chimie organique

Issam Hanna, Valérie Michaut. 1,4-Dioxene in organic synthesis: Rapid access to the oxabicyclo[4.2.1]nonene system. Organic Letters, 2000, 2 (8), pp.1141-1143. ⟨10.1021/ol005718y⟩. ⟨hal-00954888⟩