Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement

Jason E. Camp; Donald Craig

doi:10.1016/j.tetlet.2009.03.091

Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement

Jason E. Camp, Donald Craig

Imperial College London

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

17 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 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
Externally published	Yes

Access to Document

10.1016/j.tetlet.2009.03.091Licence: Unspecified

Cite this

@article{b554ff158018463791432028a8ede0a0,

title = "Reactivity of dearomatised furans synthesised 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 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.",

keywords = "Aldol, Claisen rearrangement, Heteroaromatic, Microwave-assisted synthesis, Polysubstituted furan",

author = "Camp, \{Jason E.\} and Donald Craig",

year = "2009",

month = jul,

day = "1",

doi = "10.1016/j.tetlet.2009.03.091",

language = "English",

volume = "50",

pages = "3503--3508",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "26",

}

TY - JOUR

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

AU - Camp, Jason E.

AU - Craig, Donald

PY - 2009/7/1

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 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.

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 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.

KW - Aldol

KW - Claisen rearrangement

KW - Heteroaromatic

KW - Microwave-assisted synthesis

KW - Polysubstituted furan

UR - https://www.scopus.com/pages/publications/65549153765

UR - https://www.journals.elsevier.com/tetrahedron-letters

U2 - 10.1016/j.tetlet.2009.03.091

DO - 10.1016/j.tetlet.2009.03.091

M3 - Article

AN - SCOPUS:65549153765

SN - 0040-4039

VL - 50

SP - 3503

EP - 3508

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement

Abstract

Access to Document

Other files and links

Fingerprint

Cite this