Gold-catalysed cascade rearrangements of ynamide propargyl esters

Stephen J. Heffernan; James M. Beddoes; Mary F. Mahon; Alan J. Hennessy; David R. Carbery

doi:10.1039/c3cc00273j

Gold-catalysed cascade rearrangements of ynamide propargyl esters

Stephen J. Heffernan
, James M. Beddoes
, Mary F. Mahon
, Alan J. Hennessy
, David R. Carbery

Department of Chemistry

GlaxoSmithKline

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

27 Citations (SciVal)

345 Downloads (Pure)

Abstract

The Au(I)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good yield and excellent E-stereoselectivity.

Original language	English
Pages (from-to)	2314-2316
Journal	Chemical Communications
Volume	49
Issue number	23
Early online date	7 Feb 2013
DOIs	https://doi.org/10.1039/c3cc00273j
Publication status	Published - 2013

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title = "Gold-catalysed cascade rearrangements of ynamide propargyl esters",

abstract = "The Au(I)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good yield and excellent E-stereoselectivity.",

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AU - Heffernan, Stephen J.

AU - Beddoes, James M.

AU - Mahon, Mary F.

AU - Hennessy, Alan J.

AU - Carbery, David R.

PY - 2013

Y1 - 2013

N2 - The Au(I)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good yield and excellent E-stereoselectivity.

AB - The Au(I)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good yield and excellent E-stereoselectivity.

UR - https://www.scopus.com/pages/publications/84875922032

UR - http://dx.doi.org/10.1039/c3cc00273j

U2 - 10.1039/c3cc00273j

DO - 10.1039/c3cc00273j

M3 - Article

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VL - 49

SP - 2314

EP - 2316

JO - Chemical Communications

JF - Chemical Communications

IS - 23

ER -

Gold-catalysed cascade rearrangements of ynamide propargyl esters

Abstract

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