Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement

Jason E. Camp, Donald Craig

Research output: Contribution to journalArticle

15 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 dearomatised heterocycle with a variety of electrophiles gave addition products with excellent syn-diastereoselectivity. The furanol adducts were then utilised as functionalised 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
Externally publishedYes

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Furans
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2,3-dihydrofuran
furan

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Camp, Jason E. ; Craig, Donald. / Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3503-3508.
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Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement. / Camp, Jason E.; Craig, Donald.

In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3503-3508.

Research output: Contribution to journalArticle

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AU - Craig, Donald

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KW - Microwave-assisted synthesis

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