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 α-Substituted β-Amino Acids

被引：9

作者：

Stefani, Helio A. ^{[1
]}

Amaral, Monica F. Z. J. ^{[1
]}

Reyes-Rangel, Gloria ^{[2
]}

Vargas-Caporali, Jorge ^{[2
]}

Juaristi, Eusebio ^{[2
]}

机构：

[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo, Brazil

[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Mexico City 07000, DF, Mexico

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 33期

关键词：

Palladium; Borates; Cross-coupling; Nitrogen heterocycles; Amino acids; Enantioselective synthesis; N-ACYLIMINIUM IONS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-ADDITION; NATURAL-PRODUCTS; POTASSIUM; EFFICIENT; ARYL; DECARBOXYLATION; STEREOISOMERS;

D O I：

10.1002/ejoc.201000852

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6393 / 6403

页数：11

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