Practical synthesis of 4,4,4-trifluorocrotonaldehyde: a versatile precursor for the enantioselective formation of trifluoromethylated stereogenic centers via organocatalytic 1,4-additions |
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| Authors: | Shibatomi Kazutaka Narayama Akira Abe Yoshiyuki Iwasa Seiji |
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| Affiliation: | Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Toyohashi 441-8580, Japan. shiba@ens.tut.ac.jp |
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| Abstract: | 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. |
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