Malonate-type bis(oxazoline) ligands with sp2 hybridized bridge carbon: synthesis and application in Friedel–Crafts alkylation and allylic alkylation

A series of simple and new C2-symmetric diphenylmethylidene malonate-type bis(oxazoline) ligands were synthesized and applied to the Friedel–Crafts reaction and allylic alkylation. The Cu(II) complex of ligand 4b bearing the benzyl group afforded good to excellent enantioselectivity for the F–C adducts (up to >99% ee) between indole and alkylidene malonate, and the palladium complex of ligand 4c bearing the phenyl group afforded excellent enantioselectivity (up to 94% ee) for the allylic alkylation product.

A series of new and simple C2-symmetric diphenylmethylidene malonate-type bis(oxazoline) ligands were synthesized and applied to the F–C reaction and allylic alkylation. The copper complex of ligand 4b bearing benzyl group afforded good to excellent enantioselectivity for the F–C adducts (up to >99% ee). The Pd complex of ligand 4c bearing phenyl group gave up to 94% ee value for the allylic alkylation product.Figure optionsDownload as PowerPoint slide