Preparation of enantiomerically pure pyridyl amino acids from serine

Preparation of enantiomerically pure pyridyl amino acids from serine

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 r...

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Veröffentlicht in:Organic & biomolecular chemistry 2003-12, Vol.1 (23), p.4254-4261
Hauptverfasser: Tabanella, Stefania, Valancogne, Ingrid, Jackson, Richard F W
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Kinetics
Molecular Structure
Pyridines - chemistry
Serine - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b308750f