Lipase-mediated resolution of 2-hydroxymethyl-1-iodoferrocene: synthesis of ferrocenes and biferrocenes with planar chirality |
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| Affiliation: | 1. Department of Chemistry, Fatih University, 34500 B.Çekmece, Istanbul, Turkey;2. Department of Physics, Fatih University, 34500 B.Çekmece, Istanbul, Turkey;3. Department of Physics, Hitit University, 19030 Çevre Yolu Bulvarı, Çorum, Turkey;4. TUBITAK-UME, National Metrology Institute, 41470 Gebze, Kocaeli, Turkey |
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| Abstract: | Racemic 2-hydroxymethyl-1-iodoferrocene (±)-1 was subjected to esterification in the presence of lipase from Candida antarctica (Novozym® 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. |
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