Ireland-Claisen rearrangement of ynamides: Stereocontrolled synthesis of 2-amidodienes

S.J. Heffernan; D.R. Carbery

doi:10.1016/j.tetlet.2012.07.088

Ireland-Claisen rearrangement of ynamides: Stereocontrolled synthesis of 2-amidodienes

S.J. Heffernan, D.R. Carbery

Department of Chemistry

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Abstract

The Ireland-Claisen rearrangement of propargyl ynamido ester substrates is reported. The expected allenamide carboxylic acid products from [3,3]-sigmatropic rearrangement are not isolated, with 2-amidodienes alternatively formed in good yield with high levels of stereocontrol after decarboxylation.

Original language	English
Pages (from-to)	5180-5182
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.088
Publication status	Published - 19 Sept 2012

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10.1016/j.tetlet.2012.07.088

Authors' accepted version
NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 53, issue 38, 2012, DOI 10.1016/j.tetlet.2012.07.088
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abstract = "The Ireland-Claisen rearrangement of propargyl ynamido ester substrates is reported. The expected allenamide carboxylic acid products from [3,3]-sigmatropic rearrangement are not isolated, with 2-amidodienes alternatively formed in good yield with high levels of stereocontrol after decarboxylation. ",

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AU - Heffernan, S.J.

AU - Carbery, D.R.

PY - 2012/9/19

Y1 - 2012/9/19

N2 - The Ireland-Claisen rearrangement of propargyl ynamido ester substrates is reported. The expected allenamide carboxylic acid products from [3,3]-sigmatropic rearrangement are not isolated, with 2-amidodienes alternatively formed in good yield with high levels of stereocontrol after decarboxylation.

AB - The Ireland-Claisen rearrangement of propargyl ynamido ester substrates is reported. The expected allenamide carboxylic acid products from [3,3]-sigmatropic rearrangement are not isolated, with 2-amidodienes alternatively formed in good yield with high levels of stereocontrol after decarboxylation.

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M3 - Letter

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EP - 5182

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Ireland-Claisen rearrangement of ynamides: Stereocontrolled synthesis of 2-amidodienes

Abstract

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