Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement

Jason E. Camp, Donald. Craig

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The decarboxylative Claisen rearrangement (dCr) reaction of 1-(furan-2-yl)ethyl 2-tosylacetate afforded 2-ethylidene-3-(tosylmethyl)-2,3-dihydrofuran. Reaction of the dearomatized heterocycle with a variety of electrophiles gave addn. products with excellent syn-diastereoselectivity. The furanol adducts were then utilized as functionalized scaffolds for a series of subsequent transformations.
Original languageEnglish
Pages (from-to)3503-3508
Number of pages6
JournalTetrahedron Letters
Volume50
Issue number26
Early online date18 Mar 2009
DOIs
Publication statusPublished - 1 Jul 2009

Keywords

  • decarboxylative Claisen rearrangement furanylethyl tosylacetate
  • ethylidenetosylmethyldihydrofuran prepn stereoselective reaction electrophile
  • furan ethylidenetosylmethyldihydro prepn stereoselective reaction electrophile

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