Novel synthesis of alpha-trifluoromethylated alpha-amino acid derivatives from gamma-hydroxy-alpha-fluoro-alpha-trifluoromethyl carboxamides |
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| Authors: | Ogu Kenichi Matsumoto Shoji Akazome Motohiro Ogura Katsuyuki |
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| Affiliation: | Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, 1-33 Yayoicho, Inageku, Chiba 263-8522, Japan. |
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| Abstract: | On treatment with an organoaluminum reagent such as trimethylaluminum or DIBAL-H, gamma-hydroxy-alpha-fluoro-alpha-trifluoromethyl carboxamides (1) give a single diastereomer of alpha-amino-alpha-trifluoromethyl-gamma-lactones (2), which are a ring-closed form of gamma-hydroxy-alpha-trifluoromethyl-alpha-amino acids. This intriguing reaction results from intramolecular replacement of the fluorine atom on the alpha-carbon atom with the nitrogen atom of the amide group, which occurs in an SN2 manner. [reaction: see text] |
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