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Gold-catalysed cascade rearrangements of ynamide propargyl esters.

Chemical communications (Cambridge, England) (2013-02-13)
Stephen J Heffernan, James M Beddoes, Mary F Mahon, Alan J Hennessy, David R Carbery
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Indole, ≥99%
Supelco
Indole solution, 2000 μg/mL in methanol, certified reference material
Supelco
Indole, analytical standard
Sigma-Aldrich
Indole, ≥99%, FG