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

Abstract : 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.
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https://hal-polytechnique.archives-ouvertes.fr/hal-00954888
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Submitted on : Tuesday, March 11, 2014 - 9:49:56 PM
Last modification on : Thursday, December 9, 2021 - 2:26:02 PM

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

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