Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N,N′-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide
作者:Murat Aydemir、Nermin Meriç、Feyyaz Durap、Akın Baysal、Mahmut Toğrul
DOI:10.1016/j.jorganchem.2010.02.003
日期:2010.5
realized to be one of the most magnificent tools to access chiral alcohols in organic synthesis. A new chiral phosphinite compound N,N′-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide (1), has been synthesized by the reaction of chlorodiphenylphosphine with N,N′-bis[(1S)-1-benzyl-2-hydroxyethyl]ethanediamide under argon atmosphere. The oxidation of 1 with aqueous hydrogen peroxide, elemental
用手性分子催化剂对酮进行不对称转移氢化已被认为是在有机合成中获得手性醇的最宏伟的工具之一。通过氯二苯基膦与N, N'-bis的反应合成了一种新的手性次膦酸酯化合物N,N'-双[((1S)-1-苄基-2- O-(二苯基次膦酸酯)乙基]乙二酰胺(1)。在氩气气氛下的[(1 S)-1-苄基-2-羟乙基]乙二酰胺。用过氧化氢水溶液,元素硫或灰色硒在甲苯中氧化1得到相应的氧化物1a,硫化物1b和硒化物1c, 分别。通过1与[MCl 2(cod)](M:Pd 1d,Pt 1e)和[Ru(p- cymene)Cl 2 ] 2 1f反应获得Pd,Pt和Ru络合物。所有这些新的配合物都通过NMR,FT-IR光谱和微量分析进行了表征。另外,为证明其催化反应性,还研究了钌配合物1f作为乙酰苯衍生物与i PrOH的不对称转移氢化反应的催化剂。