Synthesis and application in asymmetric copper(I)-catalyzed allylic oxidation of a new chiral 1,10-phenanthroline derived from pinene

A convenient and rapid method for the preparation of chiral C2-symmetric 1,10-phenanthrolines is reported. As an example of this procedure the synthesis of new 1,10-phenanthroline (+)-7 and its 5,6-dihydro derivative (+)-6 from (−)-β-pinene is described. These ligands have been assessed in asymmetric copper(I)-catalyzed allylic oxidation of cycloalkenes affording enantioselectivities up to 71%.