Chiral Lewis Catalyzed Friedel-Crafts Alkylation Of Pyrrole With 4-oxo-Enoates

After more than 130 years,the Friedel-Crafts alkylation is still one of the most studied and most utilized reactions in organic synthesis.In this context,we document the Friedel-Crafts alkylations of pyrrole with a variety 4-oxo-Enoates.The main results are summarized as follows:â… .Chiral Lewis acid catalyzed Friedel-Crafts alkylations of pyrrole with 4-oxo-EnoatesThe effects of ligand,solvent,temperature and esters group on the pyrrole with a varity 4-oxo-Enoates reactions have been examined.Under the optimal condition 10 mol %3,3'-Br₂-BINOL-zirconium(â…£) tert-butoxide complex as catalyst in toluene,A series ofγ-ketoesters were synthesized and the yield up to 98%,ee up to 86%.â…¡.The organocatalytic asymmetric pyrrole with(E)-ethyl 4-oxo-4-phenylbut-2-enoate Friedel-Crafts alkylations reaction has been examined.A series of hydrogen-bonding donor small organic molecules crganocatalysts were texted in the reaction of pyrrole with(E)-ethyl 4-oxo-4-phenylbut-2-enoate,and the reaction could obtain good yield.All.target compounds were characterized by ¹H NMR,¹³C NMR,MS.