对映体纯螺旋二茂铁的不对称合成与手性光学性质
Asymmetric Synthesis and Chiroptical Properties of Enantiopure Helical Ferrocenes.
作者信息
Urbano Antonio, Del Hoyo Ana M, Martínez-Carrión Alicia, Carreño M Carmen
机构信息
Departamento de Química Orgánica , Universidad Autónoma de Madrid (UAM) , Cantoblanco , 28049 Madrid , Spain.
Institute for Advanced Research in Chemical Sciences (IAdChem), UAM , Cantoblanco , 28049 Madrid , Spain.
出版信息
Org Lett. 2019 Jun 21;21(12):4623-4627. doi: 10.1021/acs.orglett.9b01522. Epub 2019 Jun 5.
An enantiopure helical ferrocene ( R)-5 with five ortho-condensed aromatic rings was synthesized using a PtCl-catalyzed cycloisomerization of planar-chiral 2-ethynyl-1-(4-phenanthrenyl)ferrocene ( R)-6f, prepared in 3 steps from known enantiopure sulfinyl ferrocenyl boronic acid ( S, S)-7, as the source of planar chirality. This pentacyclic helical ferrocene showed a very high optical rotation value and strong circular dichroism (CD) signals.
使用平面手性2-乙炔基-1-(4-菲基)二茂铁（R）-6f的PtCl催化环异构化反应合成了一种具有五个邻位稠合芳香环的对映体纯螺旋二茂铁（R）-5，平面手性源为从已知的对映体纯亚砜基二茂铁硼酸（S，S）-7经三步制备得到的（R）-6f。这种五环螺旋二茂铁显示出非常高的旋光值和强烈的圆二色性（CD）信号。
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