Gold-Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon

• Published in: Angewandte Chemie International Edition Vol. 55; no. 41; pp. 12688 - 12692
• Main Authors: Jin, Hongming, Tian, Bin, Song, Xinlong, Xie, Jin, Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 04.10.2016; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aldehydes; alkynes; Aminoquinolines; carbenes; Carbon; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Conversion; Derivatives; Ethers; Functional anatomy; Gold; gold catalysis; Organic chemistry; Organic compounds; Physical Sciences; Quinoline; Quinolines; Ring opening; Science & Technology; umpolung; Versatility; INTERMOLECULAR NITRENE TRANSFER; DESIGN; 2H-AZIRINES; alkynes; umpolung; carbenes; gold catalysis; PYRIDINES; NUCLEOPHILIC NITRENOIDS; CLEAVING ENZYME; YNAMIDES; INHIBITORS; quinolines; ACCESS; SUBSTITUTED QUINOLINES
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201606043

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. All together now: 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 regiospecific and modular access to 2‐aminoquinolines and other quinoline derivatives under mild conditions and with a broad functional‐group tolerance.