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Syntheses of optically active trifluoronorcoronamic acids.
T Katagiri1, M Irie, K Uneyama
1Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan. uneyamak@cc.okayama-u.ac.jp
Organic Letters
|August 24, 2000
Summary
Syntheses of optically active trifluoronorcoronamic acid and its diastereomer were achieved. Highly stereospecific S(N)2 cyclization of gamma-cyanohydrins yielded key cyclopropyl nitriles for constructing these complex molecules.
Area of Science:
- Organic Chemistry
- Stereoselective Synthesis
Background:
- Trifluoronorcoronamic acid is a complex molecule with potential applications.
- Efficient synthetic routes are needed for optically active isomers.
Purpose of the Study:
- To describe the synthesis of optically active trifluoronorcoronamic acid and its diastereomer.
- To explore stereospecific and diastereoselective synthetic methodologies.
Main Methods:
- S(N)2 cyclization of gamma-cyanohydrins.
- Hydrolysis of cyano groups and deprotection of amino groups.
- Hofmann rearrangement and oxidative cleavage for diastereomer synthesis.
Main Results:
- Highly stereospecific and diastereoselective S(N)2 cyclization yielded cyclopropyl nitriles.
- Trifluoronorcoronamic acid was obtained through hydrolysis and deprotection.
- Trifluoro-allo-norcoronamic acid was synthesized via Hofmann rearrangement and oxidative cleavage.
Conclusions:
- The study successfully synthesized optically active trifluoronorcoronamic acid and its diastereomer.
- Stereospecific S(N)2 cyclization is an effective method for constructing key intermediates.
- The described methods provide access to valuable fluorinated amino acid derivatives.