Synthesis,Characterization and Solid-State CD Spectra of the Chiral Bisferrocenyl Ligands

Abstract

以甲酰基二茂铁(1)和手性1,2-二苯基乙二胺[(1R,2R)-1,2-二苯基乙二胺(2R),(1S,2S)-1,2-二苯基乙二胺(2S)]为原料,经缩合、还原和N-烷基化反应,制备了一对新型手性四齿双二茂铁基配体[N,N′-二(二茂铁基甲基)-N,N′-二(2-羟基丙基)-(1R,2R)-1,2-二苯基乙二胺(5R)和N,N′-二(二茂铁基甲基)-N,N′-二(2-羟基丙基)-(1S,2S)-1,2-二苯基乙二胺(5S)].用元素分析、红外(IR)、质子核磁共振(1HNMR)、紫外-可见(UV-Vis)、固体圆二色(CD)光谱等对手性产物(3R-5S)进行了表征.固体CD光谱研究表明,配体5R(或5S)的手性特征和4R(或4S)相似而与3R(或3S)却有一定差别.A pair of novel chiral tetradentate bisferrocenyl ligands [N,N'-bisferrocenylmethyl-N,N'-bis(2-hydroproxypyl)-(1R,2R)-1,2-diphenylethane-diamine(5R),N,N'-bisferrocenylmethyl-N,N'-bis(2-hydroxypropyl)-(1S,2S)-1,2-diphenylethane diamine(5S)] were synthesized from ferrocenylcarboxaldehyde(1)and chiral 1,2-diphenylethane-diamine(2R or 2S)followed by the reduction of the Schiff bases with NaBH4 and subsequent N-alkylation with 1,2-propyleneoxide.All the chiral products(3R-5S)were charactered by elemental analysis,infrared(IR),1H nuclear magnetic resonance(1H NMR),ultraviolet-visible(UV-Vis)and solid-state circular dichroism(CD)spectra.The solid-state CD spectra reveal that the chiral characteristics of 5R(or 5S)are quite similar with 4R(or 4S)and it is also notable that there are some differences between 5R(or 5S)and 3R(or 3S).国家自然科学基金(20373056);; 福建省自然科学基金(2005YZ1020);; 厦门大学科技创新项目(B类,XDKJCX20061027)资

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