Lipase-mediated resolution of 2-hydroxymethyl-1-iodoferrocene: Synthesis of ferrocenes and biferrocenes with planar chirality

Abstract

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.