Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines.
Reductive cyclization of 2-iminonitrostyrenes (from the condensation of 2-aminostyrenes with an aldehyde and subsequent nitration of the alkene) using a bifunctional thiourea catalyst and tert-butyl-Hantzsch ester leads to an intramolecular conjugate hydride addition nitro-Mannich reaction to give the corresponding cis-2-aryl-3-nitrotetrahydroquinolines as single diastereoisomers in high yields and enantioselectivities.
Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
James C
JC
Anderson
Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
Joshua P
JP
Barham
Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
Christopher D
CD
Rundell
D002384:Catalysis; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
D004952:Esters; D009574:Nitro Compounds; D011804:Quinolines; D013343:Styrenes; C542964:1,2,3,4-tetrahydroquinoline; D013890:Thiourea