Stereoselective Formation of Tetrahydrofuran Rings via Intramolecular Alkoxycarbonylation of Hydroxyalkenes

M. F. Semmelhack, Nan Zhang

Research output: Contribution to journalLetter

94 Scopus citations

Abstract

Starting from 5-hydroxy- 1-pentenes, palladium-catalyzed intramolecular alkoxycarbonylation produces 2,5-disubstituted tetrahydrofurans in good yield. In the simplest cases, mixtures of cis- and trans-2,5-substitution are obtained. With a methyl group at C-4, the mixture is 1:1 or 2:1 depending on the relative configuration of the Me. With a methyl or phenyl group at C-3, the selectivity is much higher, producing either cis-2,5- or trans-2,5-disubstituted furans in >9:1 selectivity. In the best case, with a 3-phenyl derivative, the selectivity is >99%. The formation of cis or trans isomers depends on the configuration at C-3 in a predictible way.

Original languageEnglish (US)
Pages (from-to)4483-4485
Number of pages3
JournalJournal of Organic Chemistry
Volume54
Issue number19
DOIs
StatePublished - Sep 1 1989

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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