Synthesis of chiral benzene-based tetraoxazolines and their application in asymmetric Friedel-Crafts alkylation of indole derivatives with nitroalkenes

A series of new chiral benzene-based tetraoxazoline ligands were prepared in good yields through the reaction of 1,2,4,5-benzenetetracarboxylic acid and chiral beta-amino alcohols by continuous removal of water, and the asymmetric Friedel-Crafts alkylation of indole derivatives with nitroalkenes was tested using the chiral catalysts, which were generated in situ by refluxing the above ligands and anhydrous zinc chloride in solvent. In most case, good yields (up to 99%) and excellent enantioselectivities (up to 98% ee) were obtained. (C) 2014 Elsevier B.V. All rights reserved.