Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions

Zheng Hao Tzeng, Shuen Wen Yang, Pang Min Liu, Kwunmin Chen

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)626-631
Number of pages6
JournalJournal of the Chinese Chemical Society
Volume55
Issue number3
DOIs
Publication statusPublished - 2008 Jan 1

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Carboxylic Acids
Column chromatography
Dipeptides
Valine
Esters
Amino Acids

Keywords

  • 5-Oxo-1-phenyl-pyrazolidine-3-carboxylic acid
  • L-amino acid
  • Optical resolution
  • Organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions. / Tzeng, Zheng Hao; Yang, Shuen Wen; Liu, Pang Min; Chen, Kwunmin.

In: Journal of the Chinese Chemical Society, Vol. 55, No. 3, 01.01.2008, p. 626-631.

Research output: Contribution to journalArticle

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