Fluorous Substituent‐Based Enantiomer and Diastereomer Separation: Orthogonal Use of HPLC Columns for the Synthesis of Nonproteinogenic Polyfluoro Amino Acids and Peptides

Abstract

Abstract A variety of fluorine‐containing amino acid and dipeptide precursors bearing different lengths of perfluoroalkyl chains were separated into their enantiomers and diastereomers, respectively, by the orthogonal use of fluorous and chiral HPLC columns. These results show the applicability of fluorous racemic mixture synthesis for various “fluorinated” chiral products without introducing conventional cleavable fluorous tags. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)