Racemic 2-hydroxymethyl-1-iodoferrocene (±)-1 was subjected to esterification in the presence of lipase from Candida antarctica (Novozym(R) 435) to afford (1S,2S)-2-acetoxymethyl-1-iodoferrocene (-)-2 having 89% ee and unreacted (1R,2R)-2-hydroxymethyl-1-iodoferrocene (+)-1 in enantiopure form. A single enantiomer of 2-hydroxymethyl-1-iodoferrocene gave easy access to new ferrocenes and biferrocenes possessing only planar chirality.
Patti, A., Lambusta, D., Piattelli, M., & Nicolosi, G. (1998). Lipase-mediated resolution of 2-hydroxymethyl-1-iodoferrocene: Synthesis of ferrocenes and biferrocenes with planar chirality. Tetrahedron Asymmetry, 9(17), 3073–3080. https://doi.org/10.1016/S0957-4166(98)00311-5