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An unexpected bidirectional molecular rotor from unidirectional molecular motor via a stereoselective enamine-imine tautomerization process
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-08-26 , DOI: 10.1016/j.tetlet.2020.152373
Jingpeng Xiong , Quan Li , Ming-Hua Zeng

Developing stereoselective synthetic method is very important to access chiral molecular devices. We herein demonstrate how a proton initiated stereoselective enamine-imine tautomerization converts a molecular motor into a simple rotor with high diastereoselectivity (>20:1 dr). NMR and X-ray crystallography were used to elucidate the structures of both the motor and rotor unambiguously. The activated motion of the rotor about its central single bond was studied from variable temperature NMR (293–423 K) and DFT calculations provide evidence of the origin of diastereoselectivity of enamine-imine tautomerization as well as the rotor dynamics with barrier as high as 39.3 kcal/mol. Results from our work may benefit future design towards stereocontrolled and adaptive molecular machines.



中文翻译:

单向分子马达通过立体选择性烯胺-亚胺互变异构过程产生的意外双向分子转子

发展立体选择性合成方法对获得手性分子装置非常重要。我们在本文中证明了质子引发的立体选择性烯胺-亚胺互变异构如何将分子马达转化为具有高非对映选择性(> 20:1 dr)的简单转子。NMR和X射线晶体学用于明确阐明电动机和转子的结构。通过可变温度NMR(293–423 K)研究了转子围绕其中心单键的活化运动,DFT计算提供了烯胺-亚胺互变异构非对映选择性的起源证据,以及具有高达39.3的势垒的转子动力学大卡/摩尔 我们工作的结果可能会有利于未来针对立体控制和自适应分子机器的设计。

更新日期:2020-09-20
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