Bismuth(III) triflate-catalyzed synthesis of substituted 2-alkenylfurans

Dominik Nitsch, Thorsten Bach

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22 Scopus citations

Abstract

A convergent synthesis of the title compounds is reported, which relies on a successive 2-fold SN'-type substitution reaction at methoxy-substituted propargylic acetates. The furan C3-C4 bond is presumably established by silyl enol ether attack at a propargylic cation intermediate. The resulting α-methoxyallene is intramolecularly substituted, leading to cyclization by displacement of the methoxy group (O-C2 bond formation) and to simultaneous formation of the exocyclic alkene double bond. Despite the relatively mild conditions, the reactions were complete within 5 min.

Original languageEnglish
Pages (from-to)6372-6379
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number13
DOIs
StatePublished - 3 Jul 2014

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