The diastereoselective deproto-metallation of several sugar-derived ferrocene esters using lithium-zinc bases was studied. While bis[(R)-1-phenylethyl]amino as the ligand afforded the diacetone-d-glucose-based (S P)-2-iodoferrocene ester in 91% de after iodination, the R P was synthesized from α-d-glucofuranose using 2,2,6,6-tetramethylpiperidino as the ligand. Both (R P)- and (S P)-ferrocene[1,2-c]1H-quinolin-2-one were reached by subsequent cyclizing couplings, albeit their racemization was noted. © 2012 The Royal Society of Chemistry.