title: An asymmetric organocatalytic Povarov reaction with 2-hydroxystyrenes.
abstract: An organocatalytic asymmetric three-component Povarov reaction involving 2-hydroxystyrenes has been established to provide an efficient method to access structurally diverse cis-disubstituted tetrahydroquinolines in high stereoselectivities of up to >99:1 dr and 97% ee. This protocol also provides an easy access to tetrahydroquinolines with chiral quaternary stereocenters upon using α-alkyl 2-hydroxystyrenes as substrates. The theoretical studies revealed that the Povarov reaction proceeded through a sequential vinylogous Mannich reaction and an intramolecular Friedel-Crafts reaction, wherein the phosphoric acid acted as bifunctional catalyst to activate 2-hydroxystyrene and aldimine simultaneously.
authors: School of Chemistry & Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
authors: Feng
authors: F
authors: Shi
authors: Gui-Juan
authors: GJ
authors: Xing
authors: Zhong-Lin
authors: ZL
authors: Tao
authors: Shi-Wei
authors: SW
authors: Luo
authors: Shu-Jiang
authors: SJ
authors: Tu
authors: Liu-Zhu
authors: LZ
authors: Gong
mesh_terms: D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
chemical_list: D010756:Phosphoric Acids; D011804:Quinolines; D013343:Styrenes; C542964:1,2,3,4-tetrahydroquinoline