engleski

Approaches to (R)- and (S)-1'-(1-aminoethyl)ferrocene-1-carboxylic acid derivatives

Lipase-catalyzed esterification of (± ; ; )-methyl 1'-(1-hydroxyethyl)ferrocene-1-carboxylate (4) afforded its (R)-acetate [(-)-5 ; e.e. = 99%] and (S)-(+)-4 (e.e. = 90%). Stereoretentive azidation/ amination/ acetylation of (R)-(-)-5 gave (R)-(+)-methyl 1'-(1-acetamidoethyl)ferrocene-1-carboxylate [(R)-3 ; e.e. = 98%]. In a similar way (S)-(+)-4 was converted into (S)-(-)-3 (e.e. = 84%). Both enantiomers of 3 were obtained in high chemical yields without a lost of optical purity. The title compounds can be coupled with natural amino acids and peptides on both C- and N-termini.

ferrocene chiral amino acid ; CAL-B ; resolution ; lipase-catalyzed

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