Practical synthesis of 4,4,4-trifluorocrotonaldehyde: a versatile precursor for the enantioselective formation of trifluoromethylated stereogenic centers via organocatalytic 1,4-additions.
The practical synthesis of 4,4,4-trifluorocrotonaldehyde (1) and its application to enantioselective 1,4-additions are described. The organocatalytic 1,4-addition of 1 with several nucleophiles such as heteroaromatics, alkylthiols and aldoximes afforded the corresponding products, each bearing a trifluoromethylated stereogenic center with high optical purity. A resulting product was converted into an MAO-A inhibitor, befloxatone.
Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Toyohashi 441-8580, Japan. shiba@ens.tut.ac.jp
Kazutaka
K
Shibatomi
Akira
A
Narayama
Yoshiyuki
Y
Abe
Seiji
S
Iwasa
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis; D010080:Oxazoles / Q000138:chemical synthesis; D013237:Stereoisomerism
D000447:Aldehydes; D008996:Monoamine Oxidase Inhibitors; D010080:Oxazoles; C090014:befloxatone