Synthesis of cis-4-trifluoromethyl- and cis-4-difluoromethyl-l-pyroglutamic acids

Xiao-Long Qiu; Feng-Ling Qing

doi:10.1021/jo034098m

Synthesis of cis-4-trifluoromethyl- and cis-4-difluoromethyl-l-pyroglutamic acids

J Org Chem. 2003 May 2;68(9):3614-7. doi: 10.1021/jo034098m.

Authors

Xiao-Long Qiu¹, Feng-Ling Qing

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 12713369
DOI: 10.1021/jo034098m

Abstract

Efforts to synthesize 4-trifluoromethyl- and 4-difluoromethyl-l-pyroglutamic acids are described. After many arduous efforts, we successfully synthesized our target molecules cis-4-trifluoromethyl-l-pyroglutamic acid 25 and cis-4-difluoromethyl-l-pyroglutamic acid 26 from trans-4-hydroxy-l-proline through oxidation of fluorinated prolinates with RuO(4).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Combinatorial Chemistry Techniques*
Hydrocarbons, Fluorinated / chemistry
Hydrolysis
Indicators and Reagents
Molecular Structure
Oxidation-Reduction
Pyrrolidonecarboxylic Acid / analogs & derivatives*
Pyrrolidonecarboxylic Acid / chemical synthesis*
Ruthenium Compounds / chemistry*
Stereoisomerism

Substances

Hydrocarbons, Fluorinated
Indicators and Reagents
Ruthenium Compounds
ruthenium tetraoxide
Pyrrolidonecarboxylic Acid