Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

被引：4

作者：

Miklasova, Natalia ^{[1
]}

Julinek, Ondrej ^{[2
]}

Meskova, Michaela ^{[1
]}

Setnicka, Vladimir ^{[2
]}

Urbanova, Marie ^{[3
]}

Putala, Martin ^{[1
]}

机构：

[1] Comenius Univ, Dept Organ Chem, Fac Nat Sci, Bratislava 84215, Slovakia

[2] Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague 6, Czech Republic

[3] Inst Chem Technol, Dept Phys & Measurements, CR-16628 Prague 6, Czech Republic

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 15期

关键词：

CONJUGATE ADDITION; ENANTIOSELECTIVE HYDROGENATION; MONODENTATE PHOSPHORAMIDITES; DIALKYLZINC REAGENTS; RHODIUM COMPLEXES; CHIRAL PHOSPHITES; AMINO-ACIDS; LIGANDS; SPECTROSCOPY; OLEFINS;

D O I：

10.1016/j.tetlet.2010.02.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1966 / 1970

页数：5

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