Jinks Michael A, de Juan Alberto, Denis Mathieu, Fletcher Catherine J, Galli Marzia, Jamieson Ellen M G, Modicom Florian, Zhang Zhihui, Goldup Stephen M
Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK.
Angew Chem Int Ed Engl. 2018 Nov 5;57(45):14806-14810. doi: 10.1002/anie.201808990. Epub 2018 Oct 17.
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available α-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.
其中机械键提供唯一手性中心的手性互锁分子通常在没有对机械立体化学进行控制的情况下产生。在此，我们报道了一种立体选择性方法，使用易于获得的α-氨基酸衍生的叠氮化物，以高达98:2的非对映体比例合成机械平面手性轮烷。共价手性中心的对称化产生了一种轮烷，其中机械键提供了唯一的手性元素。
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