Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement

Jason E. Camp; Donald. Craig

doi:10.1016/j.tetlet.2009.03.091

Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement

Jason E. Camp, Donald. Craig

Department of Chemistry

Imperial College London

Research output: Contribution to journal › Article › peer-review

17 Citations (SciVal)

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 language	English
Pages (from-to)	3503-3508
Number of pages	6
Journal	Tetrahedron Letters
Volume	50
Issue number	26
Early online date	18 Mar 2009
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.091
Publication status	Published - 1 Jul 2009

Bibliographical note

M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.

CAPLUS AN 2009:603551(Journal)

Keywords

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

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10.1016/j.tetlet.2009.03.091

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title = "Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement",

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. ",

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T1 - Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement

AU - Camp, Jason E.

AU - Craig, Donald.

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Y1 - 2009/7/1

N2 - 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.

AB - 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.

KW - decarboxylative Claisen rearrangement furanylethyl tosylacetate

KW - ethylidenetosylmethyldihydrofuran prepn stereoselective reaction electrophile

KW - furan ethylidenetosylmethyldihydro prepn stereoselective reaction electrophile

U2 - 10.1016/j.tetlet.2009.03.091

DO - 10.1016/j.tetlet.2009.03.091

M3 - Article

SN - 0040-4039

VL - 50

SP - 3503

EP - 3508

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement

Abstract

Bibliographical note

Keywords

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