Synthesis of chiral ferrocenyl-substituted β-amino cyclopentadienes and their complexation to transition metals

CBS reduction. of the (chloroacyl)ferrocenes 3 provides the chloro alcohols 5 with greater than or equal to 98% ee, which upon treatment with cyclopentadienides yield the chiral beta- or gamma-hydroxy cyclopentadienes 6 and 7. The hydroxyl function of 6 and 7 can, be substituted with full retention of configuration by a range of N- or S-nucleophiles, giving efficient access to the optically active linked amino-cyclopentadienyl ligands 11-13. These were complexed to an iron center, yielding a ferrocenyl diamine with a large bite angle between the nitrogen donor atoms. Furthermore the first chelating complexation. reaction to titanium is presented.