Enantiomerically pure phenanthroline or bipyridine containing macrocycles: a new class of ligands for asymmetric catalysis

New enantiomerically pure phenanthroline- and bipyridine-containing macrocycles have been synthesized by combination of the coordinating unit to inexpensive and readily available chiral templates. The catalytic properties of their Cu(I) complexes have been studied in the cyclopropanation of alkenes as test reaction. A simple structural modification of the chiral cavity allowed us to successfully control the trans or cis diastereoselectivity of the reaction.