Novel Synthesis of α-Trifluoromethylated α-Amino Acid Derivatives from γ-Hydroxy-α-fluoro-α-trifluoromethyl Carboxamides
摘要:
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 S(N)2 manner.
A synthesis of 2-exo-substituted 2-endo-aminonorbornenes: Organoaluminum-promoted nucleophilic substitution on 2-endo-acetamido-2-exo-methoxynorbornene