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Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the...

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Bibliographic Details
Main Authors: Drew, Melanie A. (Author) , Arndt, Sebastian (Author) , Richardson, Christopher (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author) , Hyland, Christopher J. T. (Author)
Format: Article (Journal)
Language:English
Published: 15 October 2019
In: Chemical communications
Year: 2019, Volume: 55, Issue: 93, Pages: 13971-13974
ISSN:1364-548X
DOI:10.1039/C9CC06241F
Online Access:Verlag, Volltext: https://doi.org/10.1039/C9CC06241F
Verlag, Volltext: https://pubs.rsc.org/en/content/articlelanding/2019/cc/c9cc06241f
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Author Notes:Melanie A. Drew, Sebastian Arndt, Christopher Richardson, Matthias Rudolph, A. Stephen K. Hashmi and Christopher J.T. Hyland
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Summary:Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.
Item Description:Gesehen am 10.01.2020
Physical Description:Online Resource
ISSN:1364-548X
DOI:10.1039/C9CC06241F

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