| Autor: |
Ogu K; Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, 1-33 Yayoicho, Inageku, Chiba 263-8522, Japan., Matsumoto S, Akazome M, Ogura K |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2005 Feb 17; Vol. 7 (4), pp. 589-92. |
| DOI: |
10.1021/ol047683y |
| Abstrakt: |
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] |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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