Practical asymmetric synthesis of beta-hydroxy-beta-trifluoromethylated ketones via the first example of the in situ generation of trifluoro-acetaldehyde and its successive asymmetric carbon-carbon bond formation reaction with chiral imines.
Not only trifluoroactaldehyde ethyl hemiacetal or hydrate but also other polyfluoroalkylaldehydes acetals or hydrates react with an equimolar amount of various chiral imines, followed by hydrolysis to produce the corresponding (S)-beta-hydroxy-beta-polyfluoroalkyl ketones in good yields with good enantioselectivities; furthermore, the ee of the products can be improved by simple recrystallization.
Funabiki
Kazumasa
K
Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu, 501-1193. kfunabik@apchem.gifu-u.ac.jp
Hashimoto
Wataru
W
Matsui
Masaki
M