Collect. Czech. Chem. Commun. 2004, 69, 330-338

Synthesis of New Chiral 1,2-Disubstituted Ferrocenes

Ivana Fleischer and Štefan Toma*

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, SK-842 15 Bratislava, Slovakia


Synthesis of six chiral 1,2-disubstituted ferrocene derivatives is described starting from (S)-{[2-(methoxymethyl)pyrrolidin-1-yl]methyl}ferrocene (2) and {[N-((1R,2S)-methoxy-1-methyl-2-phenethyl)-N-methylamino]methyl}ferrocene (3). Oxidation of the (N-substituted aminomethyl)ferrocenes with active MnO2 furnished the corresponding 2-substituted ferrocenecarbaldehydes.

Keywords: Ferrocenes; Planar chirality; Diastereoselective reactions; Ferrocenecarbaldehydes; Pyrrolidines; Oxidations.

References: 25 live references.