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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of alpha-Substituted beta-Amino Acids

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Autor(es):
Stefani, Helio A. [1] ; Amaral, Monica F. Z. J. [1] ; Reyes-Rangel, Gloria [2] ; Vargas-Caporali, Jorge [2] ; Juaristi, Eusebio [2]
Número total de Autores: 5
Afiliação do(s) autor(es):
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo - Brazil
[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Mexico City 07000, DF - Mexico
Número total de Afiliações: 2
Tipo de documento: Artigo Científico
Fonte: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2010, n. 33, p. 6393-6403, NOV 2010.
Citações Web of Science: 9
Resumo

A simple protocol for the Pd(OAc)(2)-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110 degrees C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones and aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a large variety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz, -OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenriched alpha-aryl-substituted beta-amino acids. (AU)

Processo FAPESP: 07/59404-2 - Reações entre sais de potássio de organotrifluoroboratos e espécies eletrofílicas de telúrio e haletos orgânicos
Beneficiário:Helio Alexandre Stefani
Modalidade de apoio: Auxílio à Pesquisa - Temático