An Auxiliary Approach for the Stereoselective Synthesis of Topologically Chiral Catenanes
An Auxiliary Approach for the Stereoselective Synthesis of Topologically Chiral Catenanes
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DOI：
10.1016/j.chempr.2019.03.008
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发表时间：
2019-06-13
期刊：
影响因子：
23.5
通讯作者：
Goldup, Stephen M.
中科院分区：
文献类型：
--
作者：
Denis, Mathieu;Lewis, James E. M.;Goldup, Stephen M.
链烯是一种分子，其中两个环像链条中的链环一样相互穿过，可以形成两个结构，就像一个物体和它的镜像一样，但如果单个环缺乏双侧对称性，则在其他方面相同。这些结构被描述为“拓扑手性”，因为与大多数手性分子不同，它不可能在数学拓扑学规则下将一种镜像形式转换为另一种。虽然有趣的和讨论早在1961年，到目前为止，所有的方法访问的分子只含有这种拓扑立体元素需要分离的镜像形式通过手性固定相高效液相色谱，这限制了他们的调查日期。在这里，我们提出了一个简单的方法，使用一个现成的手性信息源，使立体选择性合成拓扑手性索烃。
Catenanes, molecules in which two rings are threaded through one another like links in a chain, can form as two structures related like an object and its mirror image but otherwise identical if the individual rings lack bilateral symmetry. These structures are described as "topologically chiral" because, unlike most chiral molecules, it is not possible to convert onemirror-image form to the other under the rules of mathematical topology. Although intriguing and discussed as early as 1961, to date all methods of accessing molecules containing only this topological stereogenic element require the separation of the mirror-image forms via chiral stationary phase high-performance liquid chromatography, which has limited their investigation to date. Here, we present a simple method that uses a readily available source of chiral information to allow the stereoselective synthesis of topologically chiral catenanes.