Issue 59, 2012
From the journal:

Chemical Communications

Practical synthesis of 4,4,4-trifluorocrotonaldehyde: a versatile precursor for the enantioselective formation of trifluoromethylated stereogenic centers via organocatalytic 1,4-additions†

Kazutaka Shibatomi,*a   Akira Narayama,a   Yoshiyuki Abea  and  Seiji Iwasaa  

* Corresponding authors

a Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan
E-mail: shiba@ens.tut.ac.jp
Fax: +81 532 48 5833
Tel: +81 532 44 6810

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.

Graphical abstract: 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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Article information

DOI
https://doi.org/10.1039/C2CC32757K
Article type
Communication
Submitted
18 Apr 2012
Accepted
01 Jun 2012
First published
08 Jun 2012

Chem. Commun., 2012,48, 7380-7382

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Practical synthesis of 4,4,4-trifluorocrotonaldehyde: a versatile precursor for the enantioselective formation of trifluoromethylated stereogenic centers via organocatalytic 1,4-additions

K. Shibatomi, A. Narayama, Y. Abe and S. Iwasa, Chem. Commun., 2012, 48, 7380 DOI: 10.1039/C2CC32757K

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