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

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

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-indolin...

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Veröffentlicht in:Journal of the American Chemical Society 2005-12, Vol.127 (48), p.16804-16805
1. Verfasser: Zhang, Liming
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Sprache:eng
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Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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creator Zhang, Liming
description 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 γ-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.
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subjects Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
title Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes
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