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Ferrocene-based P-chiral amidophosphinate: stereoselective synthesis and X-ray structural study
Dalton Transactions ( IF 3.5 ) Pub Date : 2022-11-23 , DOI: 10.1039/d2dt02930h
Ruslan P Shekurov 1 , Almaz A Zagidullin 1 , Mikhail N Khrizanforov 1, 2 , Daut R Islamov 2 , Tatiana P Gerasimova 1 , Farida F Akhmatkhanova 1 , Vasily A Miluykov 1
Affiliation  

Racemic and enantiopure ferrocene-based P-chiral amidophosphinates have been simply and stereoselectively synthesized by ortho-lithiation of rac- or (R)-Ugi's amine and further reaction with amidochlorophenylphosphinate Cl–P(O)(Ph)NEt2. This is the first example of an asymmetric reaction of ortho-lithiated Ugi's amine with tetracoordinated phosphorus(V) chlorides. The structures of rac- and (R)-Ugi's amine ferrocenyl(phenyl)phosphinic acid N,N-diethylamide have been extensively studied experimentally (NMR, X-ray analysis, electrochemistry). The CV first peak refers to the oxidation of the amine fragment, which is clearly seen when (R)-Ugi's amine ferrocenyl(phenyl)phosphinic acid N,N-diethylamide reacts with anhydrous acid. The addition of two equivalents of CF3COOH leads to the protonation of nitrogen atoms, and a classical reversible wave of oxidation of Fe(II) to Fe(III) is observed.

中文翻译:

基于二茂铁的 P-手性氨基次膦酸酯:立体选择性合成和 X 射线结构研究

外消旋和对映纯二茂铁基P-手性氨基次膦酸盐已通过外消旋-或 (R)-Ugi 胺的邻并进一步与氨基氯苯基次膦酸盐 Cl-P(O)(Ph)NEt 2反应,简单且立体选择性地合成。这是邻锂化 Ugi 胺与四配位氯化磷 ( V )发生不对称反应的第一个例子。rac - and ( R )-Ugi's amine ferrocenyl(phenyl)phosphinic acid N , N的结构-二乙胺已通过实验进行了广泛研究(NMR、X 射线分析、电化学)。CV 第一个峰是指胺片段的氧化,当 ( R )-Ugi 的胺二茂铁基(苯基)次膦酸N , N-二乙酰胺与无水酸反应时可以清楚地看到这一点。添加两当量的 CF 3 COOH 导致氮原子质子化,并观察到 ​​Fe( II ) 氧化为 Fe( III ) 的经典可逆波。
更新日期:2022-11-23
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