thiourea and 1-2-3-4-tetrahydroquinoline

An enantio- and diastereoselective organocatalytic intramolecular aza-Henry (nitro-Mannich) reaction has been developed. The trans-2-aryl-3-nitro-tetrahydroquinoline products are obtained in high yields and in good enantioselectivities with a bifunctional tertiary amine-thiourea catalyst. Excellent enantioselectivities were obtained after single recrystallization of some products.

Topics: Amines; Catalysis; Crystallization; Crystallography, X-Ray; Models, Molecular; Quinolines; Stereoisomerism; Thiourea

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.

Topics: Catalysis; Cyclization; Esters; Molecular Structure; Nitro Compounds; Quinolines; Stereoisomerism; Styrenes; Thiourea

Highly enantioselective chiral bifunctional thiourea catalyzed asymmetric tandem reactions for synthesis of substituted tetrahydroquinolines are described. Substituted tetrahydroquinolines were given in good yields (up to 98%), high enantioselectivities (up to >99% ee), and diastereoselectivities (up to 20:1 dr).

Topics: Catalysis; Combinatorial Chemistry Techniques; Molecular Structure; Quinolines; Stereoisomerism; Thiourea