The enantioselective synthesis and electrochemistry of the first ferrocenyl GNA nucleosides is reported. These compounds were obtained by a Sharpless asymmetric dihydroxylation reaction of [3-(N1-thyminyl)-1-(ferrocenyl)]propene as S,R and R,S enantiomers in about 70 % yield with enantiomeric excesses of >99 % and 71 %, respectively. The absolute configurations of the chiral carbon atoms in the nucleosides were assigned by single-crystal X-ray diffraction analysis of the methyl derivatives in the solid state. The compounds were also studied with circular dichroism (CD) spectroscopy in solution. The enantiomeric relationship between the S,R and R,S isomers was confirmed by the near-mirror-image CD spectra. The redox properties of the nucleosides and their methylated derivatives were investigated using cyclic voltammetry. The cyclic voltammograms revealed reversible redox processes for the entire series of compounds at potentials of -25 mV (for nonmethylated derivatives) and 75 mV (for methylated derivatives) versus the ferrocene/ferrocenium reference redox couple.

中文翻译：

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二茂铁基GNA核苷酸：有机和有机金属异种核酸之间的桥梁。

报道了第一二茂铁基GNA核苷的对映选择性合成和电化学。这些化合物通过[3-（N1-胸苷基）-1-（二茂铁基）]丙烯的S，R和R，S对映异构体的Sharpless不对称二羟基化反应获得，收率约为70％，对映体过量> 99％和71 ％， 分别。核苷中手性碳原子的绝对构型通过固态甲基衍生物的单晶X射线衍射分析确定。还通过溶液中的圆二色性（CD）光谱研究了这些化合物。S，R和R，S异构体之间的对映体关系由近镜CD光谱证实。使用循环伏安法研究了核苷及其甲基化衍生物的氧化还原性质。