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

Authors
Hanna, I Michaut, V
Citation
I. Hanna et V. Michaut, 1,4-dioxene in organic synthesis: Rapid access to the oxabicyclo[4.2.1]nonene system, ORG LETT, 2(8), 2000, pp. 1141-1143
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
8
Year of publication
2000
Pages
1141 - 1143
Database
ISI
SICI code
1523-7060(20000420)2:8<1141:1IOSRA>2.0.ZU;2-8
Abstract
Oxidation of 2,3-disubstituted 1,4-dioxenes 3 with m-chloroperbenzoic acid in methanol followed by nucleophilic addition of allyltrimethylsilane in th e presence of TiCl4 afforded dienes 5, which have been converted to oxabicy clo[4.2.1] nonenes 8 in excellent yield by olefin ring-closing metathesis r eaction.