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Amine-Catalyzed Decarboxylative Aldol Reaction of ß-Ketocarboxylic Acids with Trifluoropyruvates.
Kawanishi, Ryouta; Hattori, Shinya; Iwasa, Seiji; Shibatomi, Kazutaka.
Afiliación
  • Kawanishi R; Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
  • Hattori S; Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
  • Iwasa S; Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan.
  • Shibatomi K; Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan. shiba@chem.tut.ac.jp.
Molecules ; 24(15)2019 Jul 30.
Article en En | MEDLINE | ID: mdl-31366138
Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C-C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary ß-ketocarboxylic acids and trifluoropyruvates proceeded smoothly to yield the corresponding aldol products in high yields and with high diastereoselectivity in the presence of a tertiary amine catalyst. In this reaction, we efficiently constructed a quaternary carbon center and an adjacent trifluoromethylated carbon center. This protocol was also extended to an enantioselective reaction with a chiral amine catalyst, and the desired product was obtained with up to 73% enantioselectivity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Carboxílicos / Alcaloides de Cinchona / Ácido Pirúvico / Aldehídos Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2019 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Suiza
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Carboxílicos / Alcaloides de Cinchona / Ácido Pirúvico / Aldehídos Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2019 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Suiza