Ferrocene-based P-chiral amidophosphinate: stereoselective synthesis and X-ray structural study,Dalton Transactions

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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 胺的邻位锂化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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