Gold‐Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon |
| |
| Authors: | M. Sc. Hongming Jin M. Sc. Bin Tian M. Sc. Xinlong Song Dr. Jin Xie Dr. Matthias Rudolph Dr. Frank Rominger Prof. Dr. A. Stephen K. Hashmi |
| |
| Affiliation: | 1. Organisch-Chemisches Institut, Universit?t Heidelberg, Heidelberg, Germany;2. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, Saudi Arabia |
| |
| Abstract: | 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. |
| |
| Keywords: | alkynes carbenes gold catalysis quinolines umpolung |
|
|
