Optical Resolution of 5-Oxo-1-Phenyl-Pyrazolidine-3-Carboxylic Acid as a New Organocatalyst for Organic Reactions

Autor:	Zheng Hao Tzeng, Kwunmin Chen, Shuen Wen Yang, Pang Min Liu
Rok vydání:	2008
Předmět:	Pyrazolidine chemistry.chemical_classification chemistry.chemical_compound Column chromatography Organic reaction Resolution (mass spectrometry) Chemistry Yield (chemistry) Carboxylic acid Diastereomer Organic chemistry General Chemistry Chiral resolution
Zdroj:	Journal of the Chinese Chemical Society. 55:626-631
ISSN:	0009-4536
DOI:	10.1002/jccs.200800091
Popis:	Optical resolution of racemic 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid 2 with L-amino acid methyl ester via the diastereomers formation was investigated. Treatment of racemic 5-oxo-1-phenylpyrazolidine-3-carboxylic acid 2 with L-valine methyl ester gave diastereomers with a total yield of 86%. The diastereomeric dipeptides can be easily separated by flash column chromatography. Acidic cleavage of the derived diastereomers gave both the optically pure (+)-(R)- and (-)-(S)-5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid ((+)-(R)-2 and (-)-(S)-2) with a total yield of 94% and 95%, respectively.
Databáze:	OpenAIRE
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