Gadolinium Chloride Catalyzed Synthesis Of Tetrahydroquinoline And Lanthanide Silylamide Catalyzed Enantioselective Synthesis Of α-Hydroxy Phosphonate

The lanthanide halide catalyzed synthesis of tetrahydroquinoline and the lanthanide silylamide catalyzed Pudovik reaction are studied in this thesis,which is composed with two parts as follows:1.Gadolinium chloride catalyzed synthesis of tetrahydroquinoline1.1 GdCl3/KI catalyzed synthesis of tetrahydroquinolineGdCl₃/KI was found to be efficient mixed catalyst for the one-pot imino Diels-Alder reaction affording tetrahydroquinolines in good to excellent yields.The combination of gadolinium chloride and potassium iodide showed much higher activity in comparison with GdCl₃ itself and the reaction could be carried out smoothly in the absence of protective gas.The catalytic mechanism was discussed.1.2 Gadolinium chloride catalyzed cis-selective synthesis of tetrahydroquinolineAn efficient methodology for the one-pot and cis-selective synthesis of pyrano- and furano[3,2-c]quinolines in the presence of catalytic amount of GdCl₃ was developed. The solvent conditions,particularly the type and amount of the solvent,were found to be the predominant factors affecting the stereoselectivity of the products.2.Lanthanide Silylamide Catalyzed Enantioselective Synthesis ofα-Hydroxy PhosphonateLanthanide tris(silyl)amide(Yb[N(SiMe₃)₂]₃),was used as catalyst for Pudovik reaction.The enantioselective synthesis ofα-hydroxy phosphonate using chiral lanthanide silylamide formed in situ was explored.