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American Chemical Society, Journal of the American Chemical Society, 48(127), p. 16804-16805, 2005

DOI: 10.1021/ja056419c

Wiley-VCH Verlag, ChemInform, 15(37), 2006

DOI: 10.1002/chin.200615108

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Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters: Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes

Journal article published in 2005 by Liming Zhang ORCID
Distributing this paper is prohibited by the publisher
Distributing this paper is prohibited by the publisher

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Abstract

The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.