1392836-25-7Relevant articles and documents
An asymmetric organocatalytic povarov reaction with 2-hydroxystyrenes
Shi, Feng,Xing, Gui-Juan,Tao, Zhong-Lin,Luo, Shi-Wei,Tu, Shu-Jiang,Gong, Liu-Zhu
experimental part, p. 6970 - 6979 (2012/10/18)
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.