Kinetic Resolution of Ferrocenyl Halides via Palladium/Chiral Norbornene Cooperative Catalysis

The development of efficient general strategy for construction of structurally diverse planar chiral ferrocenes has been attracting widespread attention in organic synthesis. Herein we report enantioselective kinetic resolution (KR) of ferrocenyl halides via palladium/chiral norbornene (Pd/NBE*) cooperative catalysis. Using simple aryl iodides and olefins as the resolution reagents, we achieved good selective zero-order KR reaction and obtained a wide range of chiral ferrocenyl halide and chiral ferrocenylphosphine oxide product with good to excellent enantioselectivities (selectivity factor up to 49). The C–I bond in the recovered ferrocenyl iodide can be efficiently converted into other functional groups, which providing a general strategy for the diversified synthesis of planar chiral ferrocene. The chiral ferrocene phosphine ligand derived from KR product was proved to be an efficient chiral ligand in Cu catalyzed asymmetric [3 + 2] cyclization.