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Org Biomol Chem. 2003 Dec 7;1(23):4254-61. Epub 2003 Oct 15.

Preparation of enantiomerically pure pyridyl amino acids from serine.

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  • 1Department of Chemistry, Dainton Building, The University of Sheffield, Sheffield, UK S3 7HF.


A range of substituted pyridyl amino acids have been prepared by palladium catalysed cross-coupling of serine-derived organozinc reagents with differently substituted halopyridines. Following this procedure a DMAP analogue has been synthesised and used as a building block in the preparation of two related tripeptides, which have been tested as catalysts in the kinetic resolution of trans-2-(N-acetylamino)cyclohexan-1-ol, resulting in modest enantioselectivity.

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