Preparation, spectroscopic characterization and crystal structures of ferrocenylalkanediols and derived acetates

(meso,dl)-3-(Ferrocenylmethyl)pentane-2,4-diol (3) was synthesized by reduction of 3-(ferrocenylmethyl)pentane-2,4-dione (2) with LiAlH4 in a good yield and corresponding monoacetate 4 and diacetate 5 were prepared. Newly prepared compounds are characterized by elemental analysis, IR and NMR spectroscopy and will be used as a substrate or standards for lipase mediated desymmetrization. The structures of 3-(ferrocenylmethyl)pentane-2,4-diol (3) and 2-(ferrocenylmethyl)propane-1,3-diol diacetate (8), which is derived from prochiral 2-(ferrocenylmethyl)propane-1,2-diol (6), were determined by X-ray crystal structure analysis. The conformation of the cyclopentadienyl rings is eclipsed in 3 and almost halfway between eclipsed and staggered in 8. One O−H⋯O hydrogen bond links the molecules of diol 3 into chains, while one weak C−H⋯π interaction self-assembles the molecules of diacetate 8 into dimers.