Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.
The first highly enantioselective synthesis of a six-membered ring quinoline catalyzed by a cationic BINAP-palladium(II) complex is shown to afford the quinoline products having a quaternary carbon center or a spiro-ring in quantitative yield and >99% ee.
Hatano
Manabu
M
Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
Mikami
Koichi
K
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D009281:Naphthalenes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000480:Alkynes; C406943:BINAP, 2-naphthol; D009281:Naphthalenes; D009942:Organometallic Compounds; D011804:Quinolines; D010165:Palladium