Synthesis of Catalytically ActiveRuthenium Complexes with a Remote Chiral Lactam as Hydrogen-BondingMotif
Synthesis of Catalytically ActiveRuthenium Complexes with a Remote Chiral Lactam as Hydrogen-BondingMotif
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以远程手性内酰胺为氢键基序的催化活性钌配合物的合成
DOI：
10.1055/s-0030-1258424
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
Voss F
中科院分区：
文献类型：
--
作者：
Voss F
末端炔通过碳碳键与构象受限的u型手性内酰胺相连，即与1,5,7 -三甲基-3-氮杂环的碳原子C7相连[3.3]。1) nonan-2-one。该炔通过Sonogashira交叉偶联与各种配体（联吡啶、三吡啶、pybox）相连。所得产物转化为四种确定的钌配合物（收率为58-94%）。该配合物含有一个具有催化活性的金属中心，该中心在空间上远离手性内酰胺的氢键基序。其中一种配合物的初步实验证明，该配合物在氧化反应中具有催化活性，并且由于底物与手性内酰胺的配位而实现了对映选择性。
A terminal alkyne was prepared, which is linked by a carbon-carbon bond to a conformationally restricted, U-shaped chiral lactam, that is, more precisely, to carbon atom C7 of 1, 5, 7-trimethyl-3-azabicyclo [3.3. 1] nonan-2-one. The alkyne was connected to various ligands (bipyridine, terpyridine, pybox) by Sonogashira cross-coupling with the respective bromides or triflates. The resulting products were converted into four defined ruthenium complexes (58-94% yield). The complexes contain a catalytically active metal center, which is spatially remote from the hydrogen-bonding motif of the chiral lactam. Preliminary experiments with one of these complexes proved that the complex shows catalytic activity in oxidation reactions and that enantioselectivity is achieved due to substrate coordination to the chiral lactam.