Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: metal-free, complementary anti- and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones.
A complete reversal of diastereoselectivity was observed for reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines, derived from propiophenones, that produce 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones. This process serves as the first reliable, metal-free, complementary anti- and syn-selective method to prepare 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones.
Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. funabiki@gifu-u.ac.jp
Kazumasa
K
Funabiki
Kei
K
Matsunaga
Hiroshi
H
Gonda
Hitoshi
H
Yamamoto
Takao
T
Arima
Yasuhiro
Y
Kubota
Masaki
M
Matsui
D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D002074:Butanones; D007097:Imines; C055298:trifluoroacetaldehyde; D000079:Acetaldehyde