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Gold catalysis: β-ketonaphthalenes via molecular gymnastics of 1,6-diyne-4-en-3-ols

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1,6-Diyne-4-en-3-ols with one terminal alkyne were applied as test substrates for a possible dual catalyzed cyclization. Instead of a dual catalysis cycle, naphthyl ketone derivatives were obtained as single products. The regioselectivity of the obtained products is unprecedented. Instead of the exp...

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Bibliographic Details
Main Authors: Lauterbach, Tobias (Author) , Arndt, Sebastian (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: June 4, 2013
In: Advanced synthesis & catalysis
Year: 2013, Volume: 355, Issue: 9, Pages: 1755-1761
ISSN:1615-4169
DOI:10.1002/adsc.201300396
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.201300396
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201300396
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Author Notes:Tobias Lauterbach, Sebastian Arndt, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:1,6-Diyne-4-en-3-ols with one terminal alkyne were applied as test substrates for a possible dual catalyzed cyclization. Instead of a dual catalysis cycle, naphthyl ketone derivatives were obtained as single products. The regioselectivity of the obtained products is unprecedented. Instead of the expected naphthyl ketones bearing the keto group in the α-position, the keto group is positioned in the ß-position of the naphthyl skeleton by a complex rearrangement of the starting materials.
Item Description:Gesehen am 27.10.2021
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201300396

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