Cover Image

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...

Full description

Saved in:
Bibliographic Details
Main Authors: Jin, Hongming (Author) , Tian, Bin (Author) , Song, Xinglong (Author) , Xie, Jin (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 27 September 2016
In: Angewandte Chemie. International edition
Year: 2016, Volume: 55, Issue: 41, Pages: 12688-12692
ISSN:1521-3773
DOI:10.1002/anie.201606043
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201606043
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/anie.201606043/abstract
Get full text
Author Notes:Hongming Jin, Bin Tian, Xinlong Song, Jin Xie, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Description
Summary: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.
Item Description:Gesehen am 25.08.2017
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201606043

Similar Items