Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions

被引：18

作者：

Wojaczynska, Elzbieta ^{[1
]}

Skarzewski, Jacek ^{[1
]}

Sidorowicz, Lukasz ^{[1
]}

Wieczorek, Robert ^{[2
]}

Wojaczynski, Jacek ^{[2
]}

机构：

[1] Wroclaw Univ Technol, Fac Chem, Dept Organ Chem, Wybrzeze Wyspianskiego 27, PL-50370 Wroclaw, Poland

[2] Univ Wroclaw, Dept Chem, 14 F Joliot Curie St, PL-50383 Wroclaw, Poland

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 11期

关键词：

TRANSITION-METAL-COMPLEXES; ENANTIOSELECTIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; NATURAL ALDOLASES; ACID-DERIVATIVES; ZN2+ COMPLEXES; LIGANDS; 1,10-PHENANTHROLINE-2,9-DICARBOXALDEHYDE; COORDINATION; COPPER(II);

D O I：

10.1039/c6nj02251k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral scaffolds of 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane were used for the construction of new modular catalysts containing complexing moieties pyridine, 2,2'-bipyridine and 1,10-phenanthroline appended by an imine linkage. The coordination abilities of the new ligands towards Zn(II) were investigated using NMR and UV spectroscopy. The plausible structures of the [ZnL2](2+) and [ZnLXn]((2-n)+) complexes formed were established by comparison of the experimental and DFT-calculated NMR spectra. The catalytic application of the [ZnLXn]((2-n)+)-type complexes in the asymmetric aldol reaction of ketones with aromatic aldehydes produced an excess of the respective syn-aldols in up to >98% ee.

引用

页码：9795 / 9805

页数：11

共 52 条

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