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Chirality. 2012 Dec;24(12):1082-91. doi: 10.1002/chir.22101. Epub 2012 Sep 20.

Access to enantiomerically pure cis- and trans-β-phenylproline by high-performance liquid chromatography resolution.

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Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea, CSIC-Universidad de Zaragoza, Spain.


The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the β carbon either cis or trans to the carboxylic acid (cis- and trans-β-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-β-phenylproline and trans-β-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250 × 20 mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-β-phenylproline precursors.

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