Tetrahedron Letters

Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement

JE Camp, D Craig

Index: Camp, Jason E.; Craig, Donald Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3503 - 3508

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Citation Number: 13

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.