High‐Yield Diastereoselective Synthesis of Planar Chiral [2]‐ and [3]Rotaxanes Constructed from per‐Ethylated Pillar[5]arene and Pyridinium Derivatives
作者:Tomoki Ogoshi、Daiki Yamafuji、Takamichi Aoki、Keisuke Kitajima、Tada‐aki Yamagishi、Yoshihiro Hayashi、Susumu Kawauchi
DOI:10.1002/chem.201200122
日期:2012.6.11
Planar chiral [2]‐ and [3]rotaxanes constructed from pillar[5]arenes as wheels and pyridinium derivatives as axles were obtained in high yield using click reactions. The process of rotaxane formation was diastereoselective; the obtained [2]rotaxane was a racemic mixture consisting of (pS, pS, pS, pS, pS) and (pR, pR, pR, pR, pR) forms of the per‐ethylated pillar[5]arene (C2) wheel, and other possible
使用点击反应以高产率获得了由柱[5]芳烃作为轮和吡啶衍生物作为轴构建的平面手性[2]-和[3]轮烷。轮烷的形成过程是非对映选择性的;得到的 [2] 轮烷是一种外消旋混合物,由 ( pS , pS , pS , pS , pS ) 和 ( pR , pR , pR , pR , pR ) 形式的全乙基化柱[5]芳烃 ( C2 ) 轮组成和其他可能类型的 [2] 轮烷没有形成。单轴通过 ( pS , pS, pS , pS , pS ) -C2或 ( pR , pR , pR , pR , pR ) -C2车轮完成。此外,通过将两个假 [2] 轮烷连接到双功能接头上,成功合成了基于柱 [5] 芳烃的 [3] 轮烷。[3]轮烷以 1:2:1 的混合物形成,一个轴穿过两个 ( pS , pS , pS , pS , pS ) -C2 , 一个 ( pS , pS , pS , pS, pS )- C2和一个