Enantioselective synthesis of planar chiral [Cr(eta(6)-arene)(CO)(3)] complexes via nucleophilic addition hydride abstraction

Non-racemic, planar chiral 1,2-disubstituted [Cr(eta(6)-arene)(CO)(3)] complexes were obtained via external chiral ligand-controlled nucleophilic addition of alkyl-, vinyl-, and aryllithium reagents to monosubstituted complexes followed by an endo-hydride abstraction with trityl cation. The reactions with [Cr(CO)(3)(eta(6)-phenyloxazoline)], [Cr(CO)(3)(eta(6)-phenylmethaneimine)], and [Cr(CO)(3)(eta(6)-phenylmethanehydrazone)] took place with complete ortho-selectivity and a high degree of enantioselectivity (up to 98% ee).