期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 13, 页码 4954-4959出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1006838
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资金
- Royal Society Wolfson
- EPSRC [EP/H021620/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H021620/1] Funding Source: researchfish
We describe a strategy for assembling different macrocycles onto a nonsymmetrical rotaxane thread in a precise sequence. If the macrocycles are small and rigid enough so that they cannot pass each other then the sequence is maintained mechanically, affording stereoisomerism in a manner reminiscent of atropisomerism. The method is exemplified through the synthesis of a pair of [3]rotaxane diastereomers that are constitutionally identical other than for the sequence of the different macrocycles on the thread. The synthesis features the iterative binding of different palladium(II) pyridine-2,6-dicarboxamide complexes to a pyridine ligand on the thread followed by their macrocyclization by ring-closing olefin metathesis. Removal of the palladium(II) from the first rotaxane formed frees the pyridine site to coordinate to a second, different, palladium(II) pyridine-2,6-dicarboxamide unit which, following macrocyclization, provides a multiring rotaxane of predetermined macrocycle sequence.
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