Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene
Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene
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DOI：
10.1021/acs.joc.7b00486
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发表时间：
2017-06-02
影响因子：
3.6
通讯作者：
Watanabe, Soichiro
中科院分区：
文献类型：
--
作者：
Saito, Hiromu;Uchida, Akira;Watanabe, Soichiro
通过消除和氧化光环化反应合成了三叶螺旋桨状三[5]-螺烯，产率分别为37%和63%。色谱纯化得到非对映异构体的混合物;并且PPM和PMM异构体在室温下逐渐转化为药物学上更稳定的PPP和MAIM异构体。确定了PPP和MMM异构体外消旋化的活化参数，并通过X射线晶体学分析确定了三[5]螺旋烯的结构。
Three-bladed propeller-shaped triple [5]-helicene was synthesized using eliminative and oxidative photocyclization reactions, which proceeded in 37 and 63% yields, respectively. Chromatographic purification gave a Mixture of diastereomers; and the PPM and PMM isomers were gradually converted to the thermodynamically more stable PPP and MAIM isomers at room temperature. The activation parameters for the racemization of the PPP and MMM isomers were determihed, and the structure of the triple [5]helicene was determined by X-ray crystallographic analysis.