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Issue 23, 2003
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Preparation of enantiomerically pure pyridyl amino acids from serine

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Abstract

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.

Graphical abstract: Preparation of enantiomerically pure pyridyl amino acids from serine

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Publication details

The article was received on 28 Jul 2003, accepted on 23 Sep 2003 and first published on 15 Oct 2003


Article type: Paper
DOI: 10.1039/B308750F
Citation: Org. Biomol. Chem., 2003,1, 4254-4261
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    Preparation of enantiomerically pure pyridyl amino acids from serine

    S. Tabanella, I. Valancogne and R. F. W. Jackson, Org. Biomol. Chem., 2003, 1, 4254
    DOI: 10.1039/B308750F

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