Issue 23, 2013
From the journal:

Chemical Communications

Gold-catalysed cascade rearrangements of ynamide propargyl esters†

Stephen J. Heffernan,‡a   James M. Beddoes,a   Mary F. Mahon,a   Alan J. Hennessyb  and  David R. Carbery*a  

* Corresponding authors

a Department of Chemistry, University of Bath, Claverton Down, UK
E-mail: d.carbery@bath.ac.uk
Tel: +44 1225 386144

b GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, UK

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.

Graphical abstract: Gold-catalysed cascade rearrangements of ynamide propargyl esters

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Article information

DOI
https://doi.org/10.1039/C3CC00273J
Article type
Communication
Submitted
12 Jan 2013
Accepted
06 Feb 2013
First published
07 Feb 2013

Chem. Commun., 2013,49, 2314-2316

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Gold-catalysed cascade rearrangements of ynamide propargyl esters

S. J. Heffernan, J. M. Beddoes, M. F. Mahon, A. J. Hennessy and D. R. Carbery, Chem. Commun., 2013, 49, 2314 DOI: 10.1039/C3CC00273J

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