Practical asymmetric synthesis of beta-trichloromethyl-beta-hydroxy ketones by the reaction of chloral or chloral hydrate with chiral imines.
[reaction: see text] Chloral or its hydrate undergoes the carbon-carbon bond-formation reaction with various optically active imines in the absence of any additive, followed by hydrolysis, to produce the corresponding beta-trichloromethyl-beta-hydroxy ketones in good yields with high enantioselectivities. In addition, the products with higher ee values were obtained by a simple recrystallization process.
Funabiki
Kazumasa
K
Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1, Yanagido, Gifu 501-1193, Japan. kfunabik@apchem.gifu-u.ac.jp
Honma
Norihiro
N
Hashimoto
Wataru
W
Matsui
Masaki
M
D002697:Chloral Hydrate / Q000031:analogs & derivatives* / Q000737:chemistry*; D003460:Crystallization / Q000379:methods; D015195:Drug Design; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000379:methods
D006843:Hydrocarbons, Chlorinated; D007097:Imines; D007659:Ketones; D012997:Solvents; D002697:Chloral Hydrate; C021100:trichloroacetaldehyde