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Gold-catalyzed synthesis of quinolines from propargyl silyl ethers and anthranils through the umpolung of a gold carbene carbon

A gold-catalyzed cascade annulation of propargylic silyl ethers with anthranils proceeds through a sequential ring opening/1,2-H-shift/protodeauration/Mukaiyama aldol cyclization. This method offers a regiospecific and modular access to 2-aminoquinolines and other quinoline derivatives under mild co...

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Bibliographische Detailangaben
Hauptverfasser: Jin, Hongming (Verfasst von) , Tian, Bin (Verfasst von) , Song, Xinglong (Verfasst von) , Xie, Jin (Verfasst von) , Rudolph, Matthias (Verfasst von) , Rominger, Frank (Verfasst von) , Hashmi, A. Stephen K. (Verfasst von)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 27 September 2016
In: Angewandte Chemie. International edition
Year: 2016, Jahrgang: 55, Heft: 41, Pages: 12688-12692
ISSN:1521-3773
DOI:10.1002/anie.201606043
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201606043
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/anie.201606043/abstract
Volltext
Verfasserangaben:Hongming Jin, Bin Tian, Xinlong Song, Jin Xie, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:A gold-catalyzed cascade annulation of propargylic silyl ethers with anthranils proceeds through a sequential ring opening/1,2-H-shift/protodeauration/Mukaiyama aldol cyclization. This method offers a regiospecific and modular access to 2-aminoquinolines and other quinoline derivatives under mild conditions and with a broad functional-group tolerance. The conversion is possible on a gram scale, which underlines the synthetic practicability of this methodology. The versatility of the obtained scaffold has been demonstrated by useful postfunctionalization.
Beschreibung:Gesehen am 25.08.2017
Beschreibung:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201606043

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