期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 19, 页码 6049-6052出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03394
关键词
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资金
- Engineering and Physical Sciences Research Council [EP/P027067/1]
- Xunta de Galicia
- European Social Fund
- EPSRC [EP/P027067/1] Funding Source: UKRI
We report the synthesis of crown ether-ammonium, amide and amine [2]rotaxanes via transition state stabilization of axle-forming reactions. In contrast to the two-step clipping and capping strategies generally used for rotaxane synthesis, here the components assemble into the interlocked molecule in a single, reagent-less, step under kinetic control. The crown ether accelerates the reaction of the axle-forming components through the cavity to give the threaded product in a form of metal-free active template synthesis. Rotaxane formation can proceed through the stabilization of different transition states featuring 5-coordinate (e.g., S(N)2) or 4-coordinate (e.g., acylation, Michael addition) carbon. Examples prepared using the approach include crown-ether-peptide rotaxanes and switchable molecular shuttles.
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