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 related tripeptides, which have been tested as catalysts in the kinetic resolution of trans-2-(N-acetylamino)cyclohexan-1-ol, resulting in modest enantioselectivity.
Tabanella
Stefania
S
Department of Chemistry, Dainton Building, The University of Sheffield, Sheffield, UK S3 7HF.
Valancogne
Ingrid
I
Jackson
Richard F W
RF
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D011725:Pyridines; D012694:Serine; C023666:pyridine