| Full text | |
| Author(s): |
Stefani, Helio A.
[1]
;
Amaral, Monica F. Z. J.
[1]
;
Reyes-Rangel, Gloria
[2]
;
Vargas-Caporali, Jorge
[2]
;
Juaristi, Eusebio
[2]
Total Authors: 5
|
| Affiliation: | [1] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo - Brazil
[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Mexico City 07000, DF - Mexico
Total Affiliations: 2
|
| Document type: | Journal article |
| Source: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2010, n. 33, p. 6393-6403, NOV 2010. |
| Web of Science Citations: | 9 |
| Abstract | |
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) | |